He signed a short-term deal with Clyde until the end of the season in April 2009. 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. 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, 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. He joined Dumbarton in March 2013. Winters signed for Rossvale in August 2014 and scored two goals on his debut. He then signed for Pollok in April 2015, where he joined his younger brother David. He joined Lowland League team East Kilbride in July 2015, but left the club the following month after "a difference of opinion" with manager Billy Ogilvie. Returning to Junior football, he made one appearance assisting Kilbirnie Ladeside before rejoining Pollok in September 2015. 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. 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. 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. Winters joined Cumbernauld United in August 2017. He retired from playing in 2018. International Winters has one Scotland cap, when he appeared as a substitute in the 1–0 friendly win against Germany in Bremen, April 1999. Career statistics Honours Dundee United Scottish Premier Division Play-offs: 1996 Scottish First Division: Runner up 1995–96 Scottish Challenge Cup: Runner up 1995–96 Scottish League Cup: Runner-up 1997–98 Aberdeen Scottish Cup: Runner-up 1999–2000 Scottish League Cup: Runner-up 1999–2000 SK Brann Norwegian Premier League: 2007 Runner-up 2006 Norwegian Cup: 2004 Livingston Scottish Second Division: 2010–11 Scottish Third Division: 2009–10 Alloa