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Conception (1994–95)
Promoters Michael Baker and Wes Smith first conceived the idea for a legends game in 1994, the same year that the pair established their business Baker Smith Management. The pair supposedly received assurance from the Australian Football League that it would make room for the game in its centenary season schedule, but this never eventuated. As such, Baker Smith pushed ahead with the match themselves, without the backing of the league.

Inaugural match and television broadcast clash (1996–98)
The inaugural match in 1996 featured squads of over 40 players from which newspaper readers could vote for the final representatives on each team. Captains Doug Hawkins and Brad Hardie led out Victoria and the All-Stars respectively, with the coaching reins being taken by Bob Skilton and Mal Brown. The All-Stars won by 14 points, and Mark Mickan took best-on-ground honours in a match that attracted 9,000 people to the Whitten Oval in Footscray. Scheduled on the Friday night of state-of-origin week, the television broadcast hit a peak rating of 30, which would be topped only by that year's AFL grand final for viewership. The following year's match courted controversy when Seven, the official broadcaster of the AFL, shifted the state-of-origin contest between Western Australia and the Allies to a day earlier, directly opposing the legends game being broadcast on rival network Nine. Peak television ratings for the charity match more than doubled that of the actual competitive football game that took place concurrently.

Despite the ratings defeat, Seven opted for the same tactic the following year, this time pitting the Allies' match at home to Victoria in a match-up that largely resembled its charity counterpart. This tactic infuriated state-of-origin officials including opposing coaches Leigh Matthews and Damian Drum, who both spoke of the supposed irony that a match honouring Ted Whitten clashed with a legitimate 'Big V' game, of which he was their biggest supporter. Nine general manager Ian Johnson described the football face-off as "a sad thing" but emphasised that the scheduling of the charity match was already locked in by the promoter months in advance. Nine executive Eddie McGuire also stoked the fire, accusing Seven of "threatening" the legend of the late Whitten – a remark strongly rebuffed by Seven head of sport Gordon Bennett – while AFL chief executive Wayne Jackson remarked that poor publicity had hurt the promotion of the state-of-origin match. As it stood, the legends game could only ever be held on the same weekend as the state-of-origin matches, due to the club and media commitments held by more than half of the competing players that would prevent them from playing at any other time. For the second year running, the Legends Game defeated the state-of-origin match in television ratings.

The match leaves Melbourne (1999–2000)
Baker Smith's agreement with the Nine Network was valid until at least 2000, with the 1999 match already tipped to be played at the Adelaide Oval – at the time, a non-league venue – by late 1998. Promoters already had one eye towards shifting the match to the soon-to-be-completed Docklands Stadium for the new millennium, however complications would arise due to Seven's base at the facilities. The standard of the match itself was improving every year, with most players recent retirees. Ted Whitten Jr. noted this increase in quality year-on-year, saying, "People were a little suspect about legends games, thinking they were not fair dinkum. But this one seems to have taken a new level." The All-Stars' two-point victory at the Adelaide Oval, a reversal of the 1998 result, squared the ledger at two wins apiece between the teams.

The 2000 match would be significant for three reasons: it ventured out of the capital cities for the first time (to Shell Stadium in Geelong), it was scheduled in the week of the AFL grand final, and it would finish in a draw, with no extra-time winner. Nine continued to use its only live Australian rules football broadcast of the year to innovate in both production and match format, given its strong interest in securing AFL coverage during the next television rights bidding process. Four goal umpires were utilised – an experiment first trialled by the AFL in the 1996 Lightning Premiership – while television cameras were positioned on the Moorabool Street side of the stadium, facing the opposite way to a regular broadcast.

Return to Melbourne and celebrity debuts (2001–03)
The battle returned to Melbourne for 2001, remaining in the AFL grand final week, where Whitten Jr. remarked at the event launch that players were now starting to train up to three months out from the match, such was the level of interest in the game. On the field, scores were tied at the end of the match again, but this time a sudden death kick-off was held to determine the eventual winner. Nominated players took set shots from 40 metres out directly in front until one team missed. During the live broadcast, commentators McGuire and Brian Taylor admitted to concocting this method of deciding the result on the fly, while hinting that the dramatic drawn finish was scripted by McGuire in his office earlier that day. This would later be seen as one of the first instances of the match veering towards sports entertainment rather than a fully-fledged even contest.

After the All-Stars went back-to-back at Optus Oval in 2002, Victoria would be without a win in five years in its preparation for the 2003 match – the first to be played under the roof at Telstra Dome. In another indication that the match was outgrowing its noble ambitions, non-football celebrities took to the field for the time in 2003, having previously acted as on-field runners. Cricket legend Shane Warne joined Victoria while he served a ban for taking an unapproved diuretic, while basketball champion Shane Heal also suited up for the Big V following his recent retirement from the Sydney Kings (which preceded his return to basketball via the San Antonio Spurs by almost three months). Actor Gary Sweet was the first celebrity to don the All-Stars guernsey in 2003, having been their runner the previous year. On-field runners Darren Berry (Victoria) and Billy Brownless (All-Stars) were miked up for Nine's broadcast, as were the coaches and umpires, the latter of which included outspoken critic Sam Newman. The scoring system was also altered for the first time, with 9-point super goals introduced after their inclusion in that year's Wizard Cup pre-season tournament – albeit from 40 metres and beyond, rather than the regular 50 metres. Victoria won the match by a point in front of 18,611 fans, with Ang Christou – fresh off retirement at Carlton and keeping fit in the hope of being signed as a punter in the National Football League – named man of the match.

Consolidation and female footballers (2004–07)
The traditional 'Big V' playing guernsey heavily associated with Whitten and state-of-origin football was worn by Victoria for the first time in 2004, with the All-Stars also donning a new design featuring an upside-down V in the red, blue and yellow colours typically worn by South Australia. Newspaper reports of the time claimed that the Victorian state jumper "hasn't been seen" since the 1999 State of Origin match between Victoria and South Australia; however, the Victorian Football League had since adopted the design from 2001 onwards for its interstate matches against fellow state leagues. Following eight consecutive matches as player for Victoria, an injured Doug Hawkins was named as coach for the 2004 match despite having never coached a game of Australian rules football before. The fixture also returned to a Friday night scheduling for the first time since 1999, taking advantage of the AFL's split round to avoid a clash with any league football.

Another indication of the growing fanfare in the Legends Game surrounded the use of guest umpires, traditionally former AFL umpires from bygone years. 2005's fixture was officiated by John Russo, Peter Cameron, Peter Carey, Mark Nash and – in a twist of irony – Phil Carman, who was once suspended for 16 weeks for headbutting an umpire. Local footballers were also given the opportunity to compete in the game for the first time, with sponsor Ray White Real Estate holding a 'Play with the Legends' wild card promotion where any registered footballer over the age of 18 could go into the draw to be selected for either team by making a $10 donation to the E. J. Whitten Foundation. Pre-game reports differed on the method of selection; one said the winners would be chosen "out of a barrel" while another written by All-Stars coach Graham Cornes proclaimed that he and rival coach Danny Frawley would have the final choices. Eventually, 37-year-old Mornington forward Simon Goosey was selected for Victoria, having once played with Geelong's reserves team back in 1990. Goosey was chosen on the back of having kicked 100 goals or more for the past nine seasons, and he would boot four majors on the night to lead the Vics to an eight-point victory. Diminutive West Australian rover Benjamin Cuming was selected as the All-Stars' wild card.

Fundraising
Promotion and news reports in the early years of the match described 'all proceeds' as being donated to the E. J. Whitten Cancer Research Foundation, and more than $100,000 was reported as being raised for prostate cancer research in the first two years of the match. Annual gala dinners were held on the night preceding the match, often at opulent venues such as the Palladium at Crown. By the week leading up to the 2000 match, a total of $230,000 had been raised since the game's inception. This figure had inflated to more than $300,000 by the time of the 2001 match, and over $360,000 a month out from the 2002 match. With the reported figure at more than $420,000 by the time of the 2003 match, the event was averaging around $60,000 towards prostate cancer research each year.

Victoria
South Melbourne champion and triple Brownlow Medallist Bob Skilton was selected as Victoria's inaugural coach for 1996, but it would be his replacement in 1998 – North Melbourne premiership player Sam Kekovich – who would coach in five consecutive years from 1998 to 2002 and hold the title for most Victorian games coached. Kekovich's sixth coaching effort in 2015 marked the longest period of time between either captaining or coaching on either team. Victoria traditionally cycled through captains in two-year stints for the majority of the event's existence; three-time Essendon premiership player Mark Harvey's three-year tenure from 2002 to 2004 saw him hold the record for most games as Victorian captain.

All-Stars
West Australian Mal Brown was selected as the All-Stars' inaugural coach in 1996. A premiership coach at South Fremantle in 1980, Brown held the coaching mantle at the All-Stars for seven consecutive years, his record unmatched by any leader on either side in the decades following. New South Welshman Terry Daniher – who played over 300 games at the highest level and captained Essendon for six seasons – held the record for the most All-Stars games captained, leading them out on five consecutive occasions from 1998 to 2002. Fellow New South Welshman Shane Crawford created history in 2014 when he became the first and only player to captain-coach a team; the role is now essentially resigned to a local football level and has not been seen in the VFL/AFL since 1981.

Celebrity players
Non-football celebrities took to the field for the first time in 2003, having previously acted as on-field runners. Cricket legend Shane Warne took the field for Victoria while he served a ban for taking an unapproved diuretic, while basketball champion Shane Heal also suited up for the Big V following his recent retirement from the Sydney Kings (which preceded his return to basketball via the San Antonio Spurs by almost three months). Actor Gary Sweet was the first celebrity to don the All-Stars guernsey in 2003, having been their runner the previous year.

Sponsorship

 * 1996–97: First National Real Estate
 * 1998: Najee
 * 1999: Siemens Mobile
 * 2000–03: Don Smallgoods
 * 2004: unknown
 * 2005–15: Ray White
 * 2016: TradingPost.com
 * 2017–18: Chemist Warehouse
 * 2019: Red Energy

Television

 * 1996–2015: Nine Network
 * 2016–19: Seven Network, Fox Footy

Radio

 * 1999(?)–2015: Triple M
 * 2016–19: Triple M, 3AW, SEN, Crocmedia

Streaming

 * 2016–18: Telstra
 * 2019: Telstra, Kayo Sports