1999 Calder Cup playoffs

The 1999 Calder Cup playoffs of the American Hockey League began on April 21, 1999. The sixteen teams that qualified, eight from each conference, played best-of-five series for division semifinals and best-of-seven series for division finals and conference finals. The conference champions played a best-of-seven series for the Calder Cup. The Calder Cup Final ended on June 13, 1999, with the Providence Bruins defeating the Rochester Americans four games to one to win the first Calder Cup in team history. Providence's Peter Ferraro won the Jack A. Butterfield Trophy as AHL playoff MVP.

Playoff seeds
After the 1998–99 AHL regular season, 16 teams qualified for the playoffs. The top four teams from each division qualified for the playoffs. However, due to the uneven number of teams in the Western Conference, it was possible for the fifth-placed team in the Empire Division to crossover to the Mid-Atlantic Division. This could only happen if the fifth-placed team in the Empire Division earned more points than the fourth-placed team in the Mid-Atlantic Division. In this case, the fifth-placed team from the Empire Division would play in place of the fourth-placed team from the Mid-Atlantic Division in that part of the playoff bracket. The Providence Bruins were the Eastern Conference regular season champions as well as the Macgregor Kilpatrick Trophy winners with the best overall regular season record. The Rochester Americans were the Western Conference regular season champions.

Atlantic Division

 * 1) Lowell Lock Monsters – 81 points
 * 2) St. John's Maple Leafs – 79 points
 * 3) Fredericton Canadiens – 77 points
 * 4) Saint John Flames – 71 points

New England Division

 * 1) Providence Bruins – Eastern Conference regular season champions; Macgregor Kilpatrick Trophy winners, 120 points
 * 2) Hartford Wolf Pack – 87 points
 * 3) Springfield Falcons – 80 points
 * 4) Worcester IceCats – 78 points

Empire Division

 * 1) Rochester Americans – Western Conference regular season champions, 111 points
 * 2) Albany River Rats – 100 points
 * 3) Hamilton Bulldogs – 91 points
 * 4) Adirondack Red Wings – 53 points

Mid-Atlantic Division

 * 1) Philadelphia Phantoms – 105 points
 * 2) Kentucky Thoroughblades – 98 points
 * 3) Hershey Bears – 85 points
 * 4) Cincinnati Mighty Ducks – 76 points

Bracket
In each round the team that earned more points during the regular season receives home ice advantage, meaning they receive the "extra" game on home-ice if the series reaches the maximum number of games. There is no set series format due to arena scheduling conflicts and travel considerations.

Division Semifinals

 * Note 1: All times are in Eastern Time (UTC−4).
 * Note 2: Game times in italics signify games to be played only if necessary.
 * Note 3: Home team is listed first.