for the 1987 season, making his debut for the club in Round 1 against at Moorabbin Oval. Having played 20 games in his debut season and kicking 37 goals, Winmar finished second in the club's best and fairest count behind Tony Lockett (who went on to win the Brownlow) and also polled 10 votes in the Brownlow Medal. In 1988, he kicked 43 goals from 21 games to be the club's leading goalkicker and again finished runner-up in the best and fairest count, this time to Danny Frawley. After an outstanding season in 1989, Winmar won St Kilda's best and fairest award and was also named in the VFL's Team of the Year on a half-forward flank. He also finished equal third in the 1989 Brownlow Medal, polling 16 votes from his 22 games. After a match against in Round 19 of the 1990 season, Winmar was suspended for 10 matches for kicking and eye-gouging Dermott Brereton. Brereton later apologised to Winmar for racially abusing him during the game. He returned to football in round seven of the 1991 season, recording 33 disposals and one goal against Adelaide at Moorabbin. Winmar's performances throughout the rest of the season led to him being named in the inaugural AFL All-Australian team. Winmar played a further 23 games in the 1992 season, including the club's semi-final loss to . At the conclusion of the season, Winmar was named the winner of the Mark of the Year competition, for a spectacular mark taken at Subiaco Oval against . In round four of the 1993 season, indigenous players Winmar and Gilbert McAdam were racially abused by Collingwood supporters, eventually being awarded two and three Brownlow Medal votes in a game St Kilda won by 22 points. The week after the game, Winmar was involved in a dispute with St Kilda over his level of pay, in particular, injury payments, and did not play for the next two weeks. Playing a total of 17 games in 1994, Winmar missed three weeks late in the season after being suspended for striking. At the end of the season, Winmar was also refused clearance by St Kilda to play in the Aboriginal All-Stars game, held at Marrara Oval in Darwin. In 1995, Winmar played in each of St Kilda's 22 games, winning the club's best and fairest award for a second time and also being named in the All-Australian