Wikipedia talk:Manual of Style/List of winningest citations

This is a list of citations and quotations relating to the usage of the word 'winningest'. I'm putting them over here to avoid making a protracted discussion page even larger and more unweildy. Most of these sources are offline or paywalled, but should be accepted per WP:AGF. I encourage everyone to take advantage of the Reference desk and The Wikipedia Library for further access and verification. Your local public libraries are very likely to also offer you access to these and many other paywalled resources. Thank you to User:Cbl62 for major expansion of this list. --Dennis Bratland (talk) 22:11, 15 January 2016 (UTC)

Style guides

 * Fowler's Concise Dictionary of Modern English Usage (First Edition)
 * "Many adjectives besides those described in 1 & 2 are capable of ordinary use, i.e. without the stylistic taint illustrated in 5 & 6, of forming a superlative in -est, used with the & serving as an emphatic form simply, while no-one would think of making a comparative in -er from them: in the brutalist, civilest, timidest, winningest, cogentest, cheerfullest, cunningest, doggiest, drunkenest, candidest, damnablest, manner. The terminations that most invite this treatment are -ful, -ing, -able, -ed, & -id; on the other hand the very common adjective terminations -ive, -ic ,& -ous, reject it altogether (curiouser & curiouser is a product of Wonderland). Though it is hard to draw a clear line between this use & the next, the intent is different; the words are felt to be little less normal & yet appreciably more forcible, than the forms with most; they are superlatives only, & emphasis is their object; an attempt is made to register them in their dictionary places."


 * Note The passage above also appears in the 1926 First Edition of Fowler's. English in Nineteenth-Century England: An Introduction by Manfred Görlach says that this is an example of Fowler's adherence to 19th Century, rather than modern, usage.

Reference type:   Subject Reference Current Version:    2015 Subject   Language reference, Usage and Grammar Guides
 * Fowler's Concise Dictionary of Modern English Usage (3 ed.)


 * See also a detailed discussion of -er and -est comparative and superlative adjective forms, with several unacceptable or exotic formations discussed, none of which is winningest.

edited by David Blair, Peter Collins
 * English in Australia

http://www.apstylebook.com.ezproxy.spl.org:2048/spl_org/?do=search_results&search_term=winningest
 * AP Stylebook Online
 * Ask the EditorQ. What is the style for "all-time winningest coach/athlete" or "coach/athlete with the most wins all-time?" Is more wordy better in this case? from Mount Pleasant, Iowa on Jun 07, 2014A. The most wins all-time is preferable. The American Heritage Dictionary lists winningest as an informal adjective.


 * H. L. Mencken The American Language


 * On the question of WP:ENGVAR and WP:TIES. H. L. Mencken discuses the special use of -er and -est adjectives as a peculiarly US American language pattern in The American Language: An Inquiry into the Development of English in the United States. A.A. Knopf, 1921 Chapter: The Common Speech pages 308-309.

Patricia T. O'Conner and Stewart Kellerman, NYT On Language columnist, author of Woe Is I: The Grammarphobe's Guide to Better English in Plain English (Riverhead, 3rd ed., 2010, ISBN 978-1-57322-331-7), Origins of the Specious Myths and Misconceptions of the English Language, The winningest dog November 4th, 2013 and in [http://www.grammarphobia.com/blog/2007/03/is-winningest-a-loser.html Is "winningest" a loser? March 6th, 2007]. "...it's a legitimate word... the adjective 'winningest' has been around for hundreds of years, first in the sense of most attractive and later in the sporting sense."
 * Patricia T. O'Conner On Language columnist, author

Britannica
(Britannica Online Reference Center) Author listed if included; not all Brittanica articles mention the author
 * Encyclopædia Britannica
 * Bobby Bowden — "Bobby Bowden, in full Robert Cleckler Bowden, (born November 8, 1929, Birmingham, Alabama, U.S.), American collegiate gridiron football coach who was one of the winningest coaches in National Collegiate Athletic Association (NCAA) history." and "pon his retirement, Bowden was second to Paterno in career wins, but he temporarily became the all-time winningest coach in 2012, when the NCAA stripped Paterno of 111 wins as punishment for a years-long sex scandal at his school." Author Adam Augustyn - Manager and Senior Editor, Encyclopædia Britannica.
 * Martin Brodeur "Martin Brodeur, (born May 6, 1972, Montreal, Quebec, Canada), Canadian ice hockey player who is the all-time winningest goaltender in the National Hockey League (NHL) with 691 career victories." and " In March 2009 Brodeur became the all-time winningest NHL goalie, passing Patrick Roy with his 552nd victory."
 * New Jersey Devils (American ice hockey team) "Although the Devils continued as one of the NHL's winningest franchises, finishing first or second in the Atlantic Division in each season of the first decade of the 2000s, they failed to return to the Stanley Cup finals that decade."
 * Wayne Embry (American basketball player and manager) "In 1985 Embry became the general manager...worked with coach Lenny Wilkens to establish the Cavaliers as one of the winningest teams in the NBA in the late '80s " Robert G. Logan - Sportswriter, Chicago Tribune. Author of The Bulls and Chicago: A Stormy Affair.
 * Phog Allen (American basketball coach) "Conference from 1929 to 1947 and now known as the Big 12). He retired as the winningest coach in college basketball. Regarded as the “father of basketball coaching …"
 * Greg Maddux (American baseball player) "He retired after the end of the 2008 season with 355 career wins, which made Maddux the second winningest pitcher in baseball's 'live-ball era' (the period that ..."
 * Sports and recreation from the article Kentucky (state, United States) "Basketball is central to the sports...Adolph Rupp , who guided the team from 1930 to 1972 and was for a long time the winningest coach in the history of college ... "  Wilford Allen Bladen - Emeritus Professor of Geography, University of Kentucky, Lexington. Author of Geography of Kentucky and Across the Appalachians. Wilma Dykeman - Adjunct Professor of English, University of Tennessee, Knoxville. State Historian of Tennessee. Author of The French Broad; coauthor of The Appalachian Mountains and others.
 * Mike Krzyzewski (American basketball coach) "In 2011 he won his 903rd career game to pass Knight as the winningest coach in Division I history. In 2014–15 Duke went 35–4 and captured a fifth national... " Adam Augustyn - Manager and Senior Editor, Encyclopædia Britannica.
 * St. Louis Cardinals (American baseball team) "Smith's Cardinal teams returned twice more...times. In 1996 the Cardinals hired manager Tony La Russa , who would go on to become the winningest manager in team history." Adam Augustyn - Manager and Senior Editor, Encyclopædia Britannica.
 * Miami Dolphins (American football team) "Despite experiencing a great deal of...career, a 38–16 loss to the San Francisco 49ers in 1985. Shula retired after the 1995 season as the winningest coach in NFL history."
 * Montreal Canadiens (Canadian hockey team) "The championship team of 1985–86 featured...and would later retire—after finishing his career with the Colorado Avalanche —as the NHL's winningest goalie of all time."
 * Bobby Allison (American stock-car racer) "Bobby Allison, byname of Robert Arthur Allison, (born December 3, 1937, Miami, Florida, U.S.), American stock-car racer who was one of the winningest drivers in National Association for Stock Car Auto Racing (NASCAR) history and a member of one of the most notable, and most tragic, families in racing. " Jay Busbee - Sportswriter, Yahoo Sports and NBC Sports Network.
 * Junior Johnson (American stock-car driver) "Johnson is also credited with inventing...purpose in NASCAR.) Johnson retired in 1966 with 50 Grand National wins, the winningest driver to have never won a..." Jay Busbee - Sportswriter, Yahoo Sports and NBC Sports Network.
 * Lee Petty (American stock-car driver) "Together with his sons, he established Petty Enterprises, a racing team which would become one of NASCAR's winningest organizations. The team was founded in .. Jay Busbee - Sportswriter, Yahoo Sports and NBC Sports Network.
 * Jim Palmer (American baseball player) "Palmer was out for most of the 1967 season...season, and problems in the early 1980s led to Baltimore releasing Palmer, their all-time winningest pitcher, in May 1984."
 * Pat Summitt (American basketball coach) "Summitt, Pat  |   née Patricia Head   (born...women's basketball coach at the University of Tennessee  (1974–2012) who was the winningest coach in the history of National..." Amy Tikkanen - Corrections Manager, Encyclopædia Britannica.
 * Joe Paterno (American football coach) "Paterno, Joe  |   byname of Joseph...who, as head coach at Pennsylvania State University  (1966–2011), was the winningest major-college coach in the history..."
 * Ole Einar Bjørndalen (Norwegian athlete) "In February 2009, when he captured his 87th World Cup win, he surpassed Swedish alpine skier Ingemar Stenmark as the winningest skier in World Cup history. In ..."
 * Gunda Niemann-Stirnemann (German athlete) "Her total of eight medals made her one of the winningest athletes in the history of the Winter Games. She retired from competitive skating in 2005. Anthony G. Craine - Independent researcher and writer.

Grolier
Explore the Encyclopedia Americana, the Grolier Multimedia Encyclopedia, The New Book of Knowledge, Lands and Peoples, and The New Book of Popular Science, and America the Beautiful.
 * Grolier Online Passport
 * Phelps, Michael (1985–   ) American competitive swimmer. "He won 7 gold medals at the 2007 World Championships, making history as the competition's winningest athlete. "  Hathaway, Ted. "Phelps, Michael (1985–    )." Encyclopedia Americana. Grolier Online, 2016. Web. 15 Jan. 2016.
 * Martina Navratilova " She eventually became the 'winningest' player in history." "Navratilova, Martina." America the Beautiful. Grolier Online, 2016. Web. 15 Jan. 2016.

Columbia
Some of these are duplicates of Brittanica; others are unique
 * Columbia Encyclopedia
 * Bobby Bowden (American football coach) "Bowden, Bobby American football coach in full Robert Cleckler Bowden November 8, 1929 Birmingham, Alabama, U.S. American collegiate gridiron football coach who was one of the winningest coaches ...
 * New Jersey Devils (American ice hockey team) "Although the Devils continued as one of the NHL’s winningest franchises, finishing first or second in the Atlantic Division in each season of the first decade of the 2000s, they failed to return to the Stanley Cup finals that decade. In 2009 Brodeur recorded his 552nd victory to become the all-time winningest goalie in the NHL. In 2009–10 the Devils topped the 40-win plateau for the 13th consecutive season, matching the record set by the Montreal Canadiens from 1971 to 1983."
 * Phog Allen (American basketball coach) "He retired as the winningest coach in college basketball."
 * Miami Dolphins (American football team) "Shula retired after the 1995 season as the winningest coach in NFL history."
 * Montreal Canadiens (Canadian hockey team) "after finishing his career with the Colorado Avalanche—as the NHL’s winningest goalie of all time."
 * Gunda Niemann-Stirnemann (German athlete) "Her total of eight medals made her one of the winningest athletes in the history of the Winter Games. She retired from competitive skating in 2005."
 * Greg Maddux (American baseball player) "He retired after the end of the 2008 season with 355 career wins, which made Maddux the second winningest pitcher in baseball’s “live-ball era” (the period that dates from the introduction of hitter-friendly rules in 1920)."
 * Sports and recreation from the article  Kentucky (state, United States) already quoted
 * Pat Summitt (American basketball coach) " American collegiate women’s basketball coach at the University of Tennessee (1974–2012) who was the winningest coach in the history of National Collegiate Athletic Association (NCAA) basketball."
 * St. Louis Cardinals (American baseball team) "In 1996 the Cardinals hired manager Tony La Russa, who would go on to become the winningest manager in team history. "
 * Defining Dementia: Year In Review 2012 (dementia) "In April 2012, less than a year after having been diagnosed with early-onset dementia, Alzheimer type, American collegiate women’s basketball coach Pat Summitt—the winningest coach in the history of NCAA basketball—retired. "
 * Sports Roundup for 2012: Year In Review 2012 (sports) "On April 18 the University of Tennessee’s Pat Summitt—the winningest basketball coach in NCAA history, with 1,098 victories—announced that she was stepping down after having been diagnosed with early-onset dementia in 2011. "
 * Football in 2010 "The Carolina Panthers had the worst record in the NFL (2–14) and at season’s end fired John Fox, the franchise’s winningest coach, who had led the Panthers to their only Super Bowl appearance after the 2003 season."
 * Joe Paterno (American football coach) "…as head coach at Pennsylvania State University (1966–2011), was the winningest major-college coach in the history of the sport, with 409 career victories, but whose accomplishments were in many ways overshadowed by a sex-abuse scandal that occurred during his tenure."
 * Ole Einar Bjørndalen (Norwegian athlete) "he surpassed Swedish alpine skier Ingemar Stenmark as the winningest skier in World Cup history. "
 * Mike Krzyzewski (American basketball coach)
 * Petty, Lee American stock-car driver March 14, 1914 Randleman, North Carolina "After retiring from racing, Petty turned his energies to the business side of the sport. Together with his sons, he established Petty Enterprises, a racing team which would become one of NASCAR’s winningest organizations. "
 * Jim Palmer (American baseball player)
 * Wayne Embry (American basketball player and manager) "and worked with coach Lenny Wilkens to establish the Cavaliers as one of the winningest teams in the NBA in the late ’80s and early ’90s, though they repeatedly fell victim in the play-offs to the great Chicago Bulls teams led by Michael Jordan. "
 * Kay Yow (American basketball coach)"was a legendary figure in women’s college basketball who served (1975–2009) as the head coach at North Carolina State University and became one of the winningest coaches in National Collegiate Athletic Association (NCAA) Division I history."
 * Bobby Allison (American stock-car racer) ", American stock-car racer who was one of the winningest drivers in National Association for Stock Car Auto Racing (NASCAR) history and a member "
 * Junior Johnson (American stock-car driver) "Johnson retired in 1966 with 50 Grand National wins, the winningest driver to have never won a championship, but he began a lucrative and heralded career as a stock-car owner. "

Encyclopaedia Judaica

 * HOLTZMAN, KENNETH DALE ("Kenny"; 1945– ), "U.S. baseball player, winningest Jewish pitcher in history." Wohlgelernter, Elli. "Holtzman, Kenneth Dale." Encyclopaedia Judaica. Ed. Michael Berenbaum and Fred Skolnik. 2nd ed. Vol. 9. Detroit: Macmillan Reference USA, 2007. 498. Gale Virtual Reference Library. Web. 15 Jan. 2016.

St. James Encyclopedia of Popular Culture
St. James Encyclopedia of Popular Culture Daryl Umberger. Ed. Thomas Riggs. Vol. 4. 2nd ed. Detroit: St. James Press, 2013.
 * Sports Heroes pp. 660-663. Word Count: 4022.
 * College Football pp. 654-656.
 * Petty, Richard (1937– ) pp. 139-140.
 * Starr, Bart (1934– ) pp. 697-698.
 * Gibson, Bob (1935– ) pp. 462-463.
 * Knight, Bobby (1940– ) pp. 190
 * Tarkanian, Jerry (1930– ) pp. 54.
 * Smith, Dean (1931– ) pp. 600
 * Shula, Don (1930– ) pp. 540-541.
 * Murray, Lenda (1962– ) pp. 668

The Scribner Encyclopedia of American Lives
The Scribner Encyclopedia of American Lives, Thematic Series: Sports Figures. Ed. Arnold Markoe and Kenneth T. Jackson. Vol. 1. New York: Charles Scribner's Sons, 2002. 392-394. Gale Virtual Reference Library. Web. 15 Jan. 2016.


 * Haskins, Donald Lee p. 392-394. Word Count: 1557. Eric Enders Vol. 1
 * Spahn, Warren Edward p. 380-382. Word Count: 1420. David Marc Vol. 2
 * Gaines, Clarence Edward, Sr. ("Bighouse") p. 312-314. Word Count: 1418. Lawson Bowling Vol. 1
 * Robinson, Edward Gay ("Eddie") p. 286-288. Word Count: 1286. J. Michael Butler Vol. 2
 * Petty, Richard Lee p. 240-242. Word Count: 1243. Kenneth Wayne Howell Vol. 2
 * Buchanan, Junious ("Buck") p. 128-130. Word Count: 1160. Michael Oriard Vol. 1
 * Longden, John Eric ("Johnny") p. 59-61. Word Count: 1126. Steven P. Savage Vol. 2

United States

 * American Heritage Dictionary
 * win·ning·est (wĭnĭng-ĭst) adj. Informal. More successful or winning more often than any others of its kind: the winningest coach in college football.
 * Merriam Webster: "having achieved the most wins "

Oxford dictionaries

 * OED
 * winning, adj.

▶ adjective esp. (US colloq.) having achieved the most success in competition.
 * The New Zealand Oxford Dictionary Edited by Tony Deverson and Graeme Kennedy Publisher: Oxford University Press Print Publication Date: 2005 Print ISBN-13:    9780195584516 Published online:  2005
 * winningest /ˈwɪnɪŋəst/

Reference type:   English Dictionary Current Version:    2004 Subject:    English Dictionaries and Thesauri ... / ˈwɪnɪŋəst / ▶ adjective US colloq. having achieved the most success in competition ....
 * Australian Oxford Dictionary (2 ed.)
 * winningest

Reference type:   English Dictionary Current Version:    2005 Subject   English Dictionaries and Thesauri ... ▶ adjective N Amer. Sport informal that has won the most often; that has recorded or achieved the most victories ....
 * The Canadian Oxford Dictionary (2 ed.)
 * winningest

Reference type:   English Dictionary Current Version:    2015 Subject:    English Dictionaries and Thesauri ... / 'wɪnɪŋɪst / ▶ adjective N. Amer. informal having achieved the most success in competition : the winningest coach in pro-football history. having achieved most success in competition winningest...
 * Oxford Dictionary of English (3 ed.)
 * winningest

Reference type:   English Dictionary Current Version:    2015 Subject:    English Dictionaries and Thesauri ... / 'winiNGist / ▶ adjective N. Amer. informal having achieved the most success in competition : the winningest coach in pro-football history. having achieved most success in competition winningest...
 * New Oxford American Dictionary (3 ed.)
 * winningest

Other

 * Online Etymology Dictionary
 * winningest "Winningest is attested by 1804."
 * Note This 1804 reference could be from the 1804 edition The False One, first published in 1647..
 * Appears in 1838 in Poems, Longer and Shorter By Thomas Burbidge
 * Earliest Google Books reference using the winningest sports figure usage in US English is from 1948


 * Google Ngram Viewer
 * comparison of winningest and most victorious


 * See also below

Slang and related dictionaries that do NOT list winningest

 * The Oxford Dictionary of New Words. Elizabeth Knowles, Julia Elliott. Elizabeth Knowles, Julia Elliott. 2, reprint, revised. Oxford University Press, 1998. the University of California. 11-Dec-09. 0198602359, 9780198602354.
 * Slang: The Topical Dictionary of Americanisms. Paul Dickson. Bloomsbury Publishing USA, 2010. 0802718493, 9780802718495. 432 pages. Reference.  › . Dictionaries.
 * The Oxford Dictionary of Slang. John Ayto. John Ayto. Oxford University Press, 1998. 019863157X, 9780198631576. 474 pages.
 * War Slang: American Fighting Words & Phrases Since the Civil War, Third Edition. Dover books on language. Paul Dickson. Courier Corporation, 2014. 0486797163, 9780486797168. 464 pages.
 * NTC's Dictionary of American Slang and Colloquial Expressions. Richard Spears. National Textbook Co. 1989 ISBN 0844254614
 * A Dictionary of Australian Colloquialisms. Gerald Alfred Wilkes. 2, illustrated, reprint. HarperCollins Publishers Australia, 1988. 0732224330, 9780732224332.
 * Dictionary of American Slang. Harold Wentworth, Stuart Berg Flexner. Harold Wentworth, Stuart Berg Flexner. 2. Crowell, 1975. 346849016X, 9783468490163.
 * American English: An Introduction. Zoltan Kovecses. Broadview Press, 2000. 1460403096, 9781460403099.
 * Cassell's Dictionary of Slang. Jonathon Green. revised. Sterling Publishing Company, Inc., 2005. 0304366366, 9780304366361.
 * Slang: The People's Poetry. Michael Adams. reprint. Oxford University Press, 2009. 0195314638, 9780195314632.
 * The Oxford Essential Dictionary of Word Histories. Glynnis Chantrell. Berkley Books, 2003. Pennsylvania State University. 29-Jun-09. 0425190986, 9780425190982.
 * The Concise New Partridge Dictionary of Slang and Unconventional English. Tom Dalzell, Terry Victor. Tom Dalzell, Terry Victor. revised. Routledge, 2014. 1317625129, 9781317625124.
 * The Columbia Guide to Standard American English. Kenneth George Wilson. Columbia University Press, 2013. 0585041482, 9780585041483.
 * The Bedford Guide for College Writers 6e With Reader, Research Manual, & Handbook C + Study Skills for College Writers. Kennedy, the Bedford Guide for College Writers, 4-In-1, Clot. Kennedy, Sidney, Dorothy M. Kennedy, X. J. Kennedy, Sylvia A. Holladay. 6. Macmillan Higher Education, 2001. 0312399510, 9780312399511. No mention of winningest in the troublesome words guide, or elsewhere

The New York Times

 * "The Winningest Football Team
 * Russell Baze, the winningest jockey in American history
 * Pettitte Finds Race Doesn't Go to the Winningest

The Wall Street Journal

 * The All-Time Winningest Yankees
 * Martin Brodeur, NHL’s Winningest Goalie, Retires
 * Coach K Becomes Winningest Coach in NCAA History

The Washington Post

 * Joe Paterno no longer winningest coach
 * Duke’s Coach Krzyzewski passes Bob Knight as winningest Division I basketball coach
 * North America's Winningest Jockey Tallies No. 10,000

The Boston Globe

 * Tim Taylor became the winningest hockey coach at Yale University
 * North Reading’s Carey becomes winningest coach with 726 victories
 * Don Nelson, NBA’s winningest coach, enters hall of fame

Chicago Tribune

 * Penn State gets wins restored, Joe Paterno again winningest coach
 * Harlem Globetrotters help honor state's winningest girls coach
 * McKenna Byrne wraps up as Timothy's winningest singles player

Chicago Sun-Times

 * Air Force flies past Texas Chicago Sun-Times January 1, 1986; 550 words "...Falcons to a 24-16 victory over Texas in the 27th Bluebonnet Bowl in Houston's Rice Stadium. The Falcons closed their winningest season at 12-1. Texas finished at 8-4. Evans, who gained 129 yards on 18 carries, was named the game's most valuable...
 * Sting's Roberts stars on defense January 10, 1986; Lacy J. Banks; 632 words " ...ability because I am a natural forward. Few, if any, other defenders can say that." Coached by Don Popovic, the MISL's winningest coach ever, the Spirit, who played the Kansas City Comets last night, are paced offensively by forward Paul Child..."
 * Bo Ryan steps down as Wisconsin’s basketball coach December 16, 2015; 534 words " ...throwing his name in the hat for the full-time gig.In more than 14 seasons at the school, Ryan is 364–130. He’s the winningest coach in Wisconsin history and took the Badgers to the NCAA Tournament in each of his 14 seasons."

Los Angeles Times

 * Jonathan Quick becomes Kings' winningest goalie in 4-0 shutout
 * The winningest football coach in Orange County history, John Barnes of Los Alamitos ...
 * The winningest coach in Villanova history, Talley is 221-133-1

The Philadelphia Inquirer

 * Paterno no longer winningest Division I coach
 * Meyer surpasses Knight as winningest coach
 * Meyer, among winningest coaches in basketball, will retire after season

Dallas Morning News

 * Scott Drew becomes all-time winningest coach at Baylor
 * Mike Petersen, Wake Forest's winningest coach, leaves ACC to coach UNT women
 * He became the winningest coach in OU history in 2013 with his 158th career victory.

Houston Chronicle

 * The area's top 5 winningest high school football programs
 * Smarr to leave Rice as college tennis' winningest coach
 * Lange takes gold, becomes winningest bobsled pilot

San Francisco Chronicle

 * Baze becomes the winningest / After slow week, jockey rides Butterfly Belle to 9,531st victory
 * Warren Spahn 1921-2003 / Winningest left-hander dies
 * Winningest team takes horrific loss

The Detroit News

 * Cook passes Cousins as MSU’s winningest QB
 * Al Fracassa: Brother Rice's revered coach is the winningest in state prep history
 * That confidence level is helped by having the winningest quarterback in program history.

Seattle Times

 * What retirement? Winningest hydro driver Dave Villwock is back at Seafair
 * Make room for Michael Phelps as winningest Olympian ever
 * Bonvicini has a career mark of 700-409 (.631), and is the 10th winningest active coach in Division I women’s basketball.

Arizona Republic

 * Vern Friedli is the winningest coach in state history
 * John MacLeod joins Ring of Honor as Phoenix Suns' winningest coach
 * State's winningest girls coach's run at Winslow coming to end

USA Today

 * With Penn State wins restored, Joe Paterno the winningest coach again

Toronto Star (largest Canadian newspaper)

 * Head coach Greg Vanney, now Toronto FC’s all-time winningest head coach with 16 victories, praised his team ...
 * With the win, Casey now has 156 career victories with the Raptors, tying him all-time with Sam Mitchell as the winningest coach in franchise history.
 * It’s a certain je ne sais quoi that makes the Arthur, Ont.-born Portuguese water dog the winningest male show dog in the history of the United States, where he now competes.

The Globe and Mail (2nd largest Canadian newspaper)

 * Mitchell becomes Raptors' winningest coach
 * Winningest jockey to ride in Queen's Plate
 * Martel now QMJHL's winningest head coach

Montreal Gazette

 * Buono winningest coach in CFL history as Lions trounce Argos
 * ... members of the Montreal club remain faithful to the iconic brand and confident of a return to glory for the winningest franchise in F1 history
 * That’s why he is the winningest U.S.-born coach in NHL history, with 446 wins and a Stanley Cup to his credit.

Older uses
Uses of the word in newspapers from the 19th and earlier 20th centuries include:
 * 1862. Boston Post Wednesday, January 15, 1862, Boston, Massachusetts "…else she was not a Coquette. And then she is daintily made (A smile from the dainty Lizette) By people expert in the trade Of forming a proper Coquette. She has the winningest ways with the beaux, (Go on!—said the winning Lizette) But there isn’t a man of them knows The mind…"
 * 1865. Farmer Bells' Thanksgiving. Centralia Sentinel. Thursday, December 21, 1865, Centralia, Illinois. "What cried the farmer, finding his voice at last. "Mine? Where'd you get it, Emily? You can't have wheeled old Grip out of a two thousand dollar mortgage for all you're the winningest bit of womankind alive. Mine Emily? Why this is the mortgage on my house!…"
 * 1906. New York Times. Sunday, April 8, 1906, New York, New York. ''"Administration. - 4 Benjamin Harrison was a man of undoubted ability, with a singularly unfortunate personality. He,had what an old countryman of mine described as * the winningest way of making men hate him ’ of any man I ever knew. He so antagonized politicians in his own party that..."...
 * 1920. Kansas City Times Saturday, July 17, 1920, Kansas City, Kansas. "Our Oil Boom Has Blown Up,” headlines the Rossviile Reporter sattly, but adds that Rossvilie may still derive a lot of satisfaction out of having one of the winningest hall teams in that part of the state. Jack Harrison of the Beloit Gazette see.s nothing remarkable in the case..."
 * 1925. Centralia Evening Sentinel Friday, December 4, 1925, Centralia, Illinois. "...sister of Mrs. Shanks of Richview. ~ The next meeting will be beld v Cd Mrs. J. M. Haney, 219 East Kerr street; The Guudry children of Los Angeles are the prize-winningest children on record. Roland Charles, 4. and Lucjenne, 5, recently went through Europe and won every children..."

Based on a search of newspapers.com, the term appears to have begun to be used in its modern usage (i.e., having the most wins in a sporting context) in the 1920s or 1930s and to have become quite widespread by the late 1940s and 1950s. Such uses from earlier years include:
 * 1930. Dubuque Telegraph Herald And Times Journal Monday, May 26, 1930, Dubuque, Iowa. "to strengthen his position as the major leagues’ winningest pitcher."
 * 1932: "Roy Spencer ... will bet dough that Bump Hadley will be the winningest twirler in Chicago White Stockings this season"
 * 1934: John McGraw - "Baseball's Winningest Pilot"
 * 1936: road trip in which White Sox won 11 of 13 games was "the 'winningest' trip" for the club in years
 * 1936: describing Vern Kennedy with 16 wins as the "Winningest Pitcher in the American League"
 * 1937: describing Frank Thomas of Alabama as "America's winningest football coach"
 * 1939: Winningest Family Has 637 Ribbons
 * 1939: Dizzy Dean "is not only a winning pitcher, but just about the winningest pitcher there is"
 * 1949: noting that the Salad Bowl featured the "winningest football team from Ohio" against the "winningest team in Arizona"
 * 1949: referring to Frank Leahy as "the winningest football coach in America"
 * 1949: describing Ann Olson, winner of 12 national championships, as "the winningest diver the United States has ever produced"
 * 1949: "America's winningest jockey, Johnny Longden, climaxed his winningest year ..."
 * 1949: with 15 victories in mid July, Vic Raschi was "the winningest pitcher in the majors"
 * 1950: describing Frank Leahy and Bud Wilkinson as "the two winningest coaches in modern American football"

Associated Press

 * Stoops Stands Alone as Oklahoma's Winningest Coach
 * College Football's Winningest Coach Retires
 * Niumatalolo will become the winningest coach in Navy history

Reuters

 * Pat Summitt, winningest college basketball coach, has dementia
 * Joe Paterno, who was fired amid a child sex abuse scandal that scarred his reputation as the winningest coach in collee football history, died Sunday.
 * Blackhawks won to "make coach Joel Quenneville into the second-winningest coach in NHL history."

UPI

 * Winningest Horse Signed For Race
 * Winningest Marks During 1960s
 * Dick Ellsworth, winningest pitcher so far this season ...

Time

 * These are the two winningest programs in Division 1 history, Kentucky with 2,089 victories in 109 seasons, and Kansas ... with 2,070 since its first season in 1899.
 * Johnny Longden ... retiring as the winningest jockey in the history of racing.
 * ... then became the winningest of them all over the next 30 years.

Newsweek

 * Woods, one of the winningest golfers of all time, is founder of the Tiger Woods Foundation, which has helped educate more than 10 million kids
 * Michigan may be the all-time winningest program in major college football (920 victories) ...
 * The winningest coach in NCAA college-basketball history did it again.

Sports Illustrated

 * At 31, Kaneda has become the winningest pitcher in Japan's pro baseball history.
 * Spurs’ Duncan, Ginobili, Parker become winningest trio in NBA history
 * John McKissick, winningest H.S. football coach, retires after 63 years

The Economist

 * The woman's touch. (jockey Julie Krone) August 14, 1993; 700+ words "...vacation's riding on you, Krone." Does Ms Krone deserve these threats? She is, as Americans put it, one of the most winningest jockeys. In June she became the first woman, anywhere in the world, to win a classic race, when in splendidly driving..."

BBC

 * 16 November, 2000. Hull sheaths Sabres once more. "Roy, the NHL's winningest goalie, made 41 saves to become the 19th player with 50 shutouts."
 * 25 October, 2003. McRae: End of the road? "Four years at Ford earned him enough victories to make the him what Americans would call the winningest rally driver of all time."
 * 3 January, 2005. College bowls round-up. "In the Outback Bowl in Tampa, David Greene, the winningest quarterback in NCAA history, enjoyed one last victory as Georgia beat Wisconsin 24-21. "
 * 15 September 2008. Matt Roberts' MotoGP round-up. Matt Roberts. BBC Sport at Indianapolis. "And it allowed Valentino Rossi - as they would say over here, the all-time winningest rider in the sport's history - to make further history as the first MotoGP winner at Indy, in what turned out to be an otherwise damp squib of a weekend."
 * 3 January 2012. Sportsday Live. "0950 AMERICAN FOOTBALL: Penn State's Joe Paterno, the 'winningest' coach in major college football history who was fired in November over a child sexual abuse scandal, died on Sunday of lung cancer. "
 * 11 August 2012. London 2012 Diary: Offbeat snippets from around the Games - day 15. "Mike Krzyzewski became 'Division I’s winningest coach' in November 2011 "
 * 11 May 2014. Eurovision 2014: Reporter's diary. Sarah Jane Griffiths Entertainment and Arts reporter, BBC News, Copenhagen. "'It just gets better for Molly!' he said this morning. 'The last song has won Eurovision six times. It's the 2nd most 'winningest' spot in the draw after 17th.' "

CBS

 * Thad Matta became the basketball program's winningest coach in a season
 * Seven Super Bowl appearances and 14 division titles for the third-winningest team in modern NFL history ...
 * Saunders is the all-time winningest coach in franchise history

NBC

 * Duncan, Parker, Ginobli Now Winningest Trio in NBA History at 541
 * Winningest coach in NCAA history retires, gets POTUS shout-out
 * Joe Paterno is, again, the winningest head coach in Div. I football history.

CBC (Canada)

 * Canadian becomes the winningest game show contestant of all time
 * Canadian becomes all-time winningest jockey
 * Devils' Martin Brodeur holds up the mesh from his team's net after becoming the winningest goaltender in history with 552 victories.

ESPN

 * John Harbaugh will wait to celebrate becoming Ravens' winningest coach
 * How Field Hockey's Winningest Coach Thrives Under Pressure
 * The NHL's all-time winningest goalie is beginning his life in hockey management