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 Netherlands national team that won the 1988 European Football Championship, but made no appearances during the final tournament.

Normally a central or holding midfielder, Winter was a hard-working and physical, yet elegant and classy team player of both quantity and quality.

Moreover, he was also deployed on either the right or left flank, as a wide midfielder, wing-back, or full-back, in particular during his time with Inter; however these were not his favoured positions, and Italian pundits did not consider him to be as well–suited to these roles due to his less convincing performances.

[6][11][12][13] Winter was also occasionally used to great effect as a centre-back under manager Guus Hiddink with the Netherlands national team, with Elko Born of Bleacher Report even ranking him as the eight–best Dutch central defender of all time in 2014.

[14] 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.

[20] Toronto won 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 succeeds Stanley Menzo, who was at the helm of the team for seven months before leaving to work at Beijing Guoan.