Club

Winters began his senior career with Dundee United in 1992 and played 118 league games for the club, scoring 27 times.^[3] 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.^[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. Playing virtually the whole match in an unfamiliar position, Winters let in four goals as Rangers beat Aberdeen 4–0.^[4]

After leaving in 2002 when his contract expired, Winters played one match for Luton Town, appearing in the first half of the first match of the season, before moving to Norway with Brann. After several seasons with hints about leaving Bergen due to family issues, Winters stated on 31 October that he no longer had the motivation needed to play for SK Brann, and that he wished to leave the club in January.^[5] He was seeking a club, preferably in Scotland, but he also stated that an English Championship club would be interesting. With no contract offer, Winters returned to SK Brann to make peace with manager Mons Ivar Mjelde and fulfil his contract until December 2007. Winters' Scottish teammate Charlie Miller did leave and subsequently joined Belgian side Lierse.

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. Winters played 178 matches for Brann, scoring 70 goals.^[6] He signed a short-term deal with Clyde until the end of the season in April 2009.^[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.^[8]

After an impressive performance as a trialist against Falkirk, Winters signed a professional contract with Livingston on 28 August 2009.

Winters played for Icelandic club Grindavík in 2011. He scored on his debut against Thor. He then played for Alloa Athletic during the 2011–12 season and helped them win the Scottish Third Division championship. In the summer of 2012, Winters signed for Peterhead,^[9] before being released in February 2013 and going on a 3-game trial with Albion Rovers. He chose not to sign a contract at the expiration of the trial.^[10] He joined Dumbarton in March 2013.^[11]

Winters signed for Rossvale in August 2014 and scored two goals on his debut.^[12] He then signed for Pollok in April 2015, where he joined his younger brother David.^[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.^[15] Returning to Junior football, he made one appearance assisting Kilbirnie Ladeside^[16] before rejoining Pollok in September 2015.^[17]

Winters came off the substitutes bench and scored with his first touch in the 2015–16 Scottish Junior Cup final for Pollok against Beith Juniors.^[18] He also scored in the penalty shootout which Pollok eventually lost. 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.^[19] However, similarly to his first spell with the side, Winters time with the club was brief and he left in November 2016, due to a combination of work commitments and a lack of playing time.^[20]

Winters joined Cumbernauld United in August 2017.^[21] He retired from playing in 2018.^[22]

International

Winters made one appearance for Scotland, in a 1–0 friendly win against Germany in Bremen, April 1999.

International