team. In the pre-season competition held prior to the start of the 1996 season, the 1996 Ansett Australia Cup, Winmar played in St Kilda's team which defeated Carlton by 58 points in the grand final held at Waverley Park and was awarded the Michael Tuck Medal as best on ground. Having damaged the medial collateral ligament of his knee in the round three game against , Winmar missed nine matches in the early part of the 1996 season before returning in the latter part of the season. Winmar played his 200th game for the club in round 17 of the 1997 season, against the at Waverley Park, becoming the first indigenous player to reach the milestone in the AFL. He also played in St Kilda's loss to Adelaide in the 1997 Grand Final, having kicked three goals against in the preliminary final the previous week. In 1998, in what was to be his last season for St Kilda, Winmar played 23 games and kicked 16 goals. He was heavily criticised during the club's match against Carlton in Round 20 after spending much of the game fighting with opponents, finishing with only eight disposals. Winmar was suspended by the club for the following match but returned to play for the club in the finals series. After the match, Winmar's manager, Peter Jess, was criticised for making comments in an interview with radio station 3AW suggesting that Aboriginal players were unable to cope with the pressures introduced by "white society". Western Bulldogs Winmar was dismissed from St Kilda at the end of the 1998 season after Tim Watson replaced Stan Alves as coach of the club. Despite being contracted for another year, the club terminated Winmar's contract as a result of his behaviour and lack of discipline over the previous season. He was then selected by the Western Bulldogs with the 30th pick overall in the 1998 National Draft, having been considered a chance to be drafted by Collingwood, North Melbourne or Carlton. Winmar played a total of 21 games for the club, kicking 34 goals, before retiring from the Western Bulldogs at the end of the 1999 season, halfway through a two-year contract, citing issues with a commitment to training and injuries. Winmar was named National Aboriginal Sportsman of the Year at the National Aboriginal and Torres Strait Islander Sports Awards held in Hobart, Tasmania, sharing the award with rugby league