Winters began his senior career with Dundee United in 1992 and played 118 league games for the club, scoring 27 times. A move to Aberdeen beckoned, which saw Billy Dodds and cash come to Tannadice in exchange for Winters. His time at Pittodrie was fruitful, with 41 goals from 132 league appearances. 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. Playing virtually the whole match in an unfamiliar position, Winters let in four goals as Rangers beat Aberdeen 4–0.