Winters has later played for Clyde, Ayr United, Livingston, Grindavik, Alloa Athletic, Peterhead and Albion Rovers.
Winters was born in East Kilbride on 4 November 1974, he played as a youth for Mallard Swifts and started his career with amateur club Muirend.
Winters began his senior career with Dundee United in 1992 and played 118 league games for the club, scoring 27 times.
[3] In the 2000 Scottish Cup Final, Winters came on as a 2nd-minute substitute to replace injured goalkeeper Jim Leighton, who suffered a fractured cheekbone.
Winters left Brann after the 2008 season, to join his family who had moved back to Scotland during the summer, due to his children starting school.
[7] Winters was released by Clyde in June 2009 along with the rest of the out of contract players, due to the club's financial position.
[13] He joined Lowland League team East Kilbride in July 2015,[14] but left the club the following month after "a difference of opinion" with manager Billy Ogilvie.
In August 2016, Winters rejoined East Kilbride for a second spell, this time in a player-coach role and was reunited with his former Rossvale manager, Martin Lauchlan.