He began his career with amateur club VV Unicum in Lelystad, moved on to SV Lelystad, and the same year joined Ajax at the age of 19. His first game for Ajax was a match against FC Utrecht on 6 April 1986, which Ajax won 3–0. Winter won two KNVB Cups (1987 and 1988), the Eredivisie title (1990), the UEFA Cup Winners' Cup (1987) and the UEFA Cup (1992)
In 1992, he moved to the Roman team Lazio, playing his first match against Sampdoria on 6 September, which Lazio tied 3–3.
In 1996, Winter joined Inter Milan, with whom he won the UEFA Cup in 1998. He had also played in the previous year's final, with the game going to penalties. However, Winter missed his penalty as Inter lost to Schalke.
Winter left Inter for his former club Ajax in 1999. In 2001, he was loaned out to Sparta Rotterdam. He played 32 games for Sparta Rotterdam and scored one goal before returning to Ajax to finish his career, and where he chose to retire in 2003.
Winter was a member of the Dutch national team that won the 1988 European Football Championship, but made no appearances during the final tournament.
In the 1994 FIFA World Cup, he scored a goal against Brazil in the quarter-finals.
He was also selected for the Dutch national team for Euro 96, as well as the 1998 FIFA World Cup in France.
Winter placed in Rijkaard's Euro 2000 squad.
Having represented his national team 84 times, scoring 6 goals, Winter is currently the twelfth most capped player for the Dutch national team.
After three years as assistant coach for the Ajax first academy team, Winter signed a three-year contract with Canadian side Toronto FC on 6 January 2011. Winter brought former colleague Bob de Klerk from Ajax to be his assistant coach, while Paul Mariner was also brought in the same day as Director of Player Development. After a disappointing season opener against Vancouver Whitecaps that ended in a 4–2 away defeat on 19 March, Winter won his first game as Toronto's head coach the following week against Portland Timbers 2–0 in Toronto.
Winter won his first trophy with Toronto in early July as Toronto defeated Vancouver 3–2 on aggregate to capture its third consecutive Canadian Championship, thereby earning a berth in the 2011–12 CONCACAF Champions League. Winter then guided Toronto to the Champions League semifinals, the first time a Canadian club had progressed that far in the competition. Toronto eventually lost 7–3 on aggregate to Santos Laguna.
However, Toronto began the 2012 MLS season with nine straight losses, the worst start to a season in the history of the MLS. Toronto managed to win its tenth match 1–0 versus Philadelphia on 26 May 2012, but it was not enough to save Winter's job, as the club announced on 7 June 2012 that he would be replaced by the director of player development, Paul Mariner.
Winter was born in Paramaribo, Suriname.As of 8 June 2012
KNVB Cup: 1986–87
UEFA Cup Winners Cup: 1986–87
UEFA Cup: 1991–92
UEFA Cup: 1997–98
UEFA European Championship: 1988
Dutch Young Player of the Year (1): 1986
Canadian Championship (2): 2011, 2012