Career
Born in Stockton-on-Tees, County Durham, Winn started his career after signing for Middlesbrough at the age of eight, before joining Oldham Athletic as a schoolboy. He made his first team debut as an 83rd minute substitute in a 1–0 defeat at Swindon Town on 16 October 2004. His second and final appearance of the 2004-2005 season came as an 88th-minute substitute in a 2–1 defeat to Bournemouth.
He was released by Oldham and signed for Conference National team York City on 29 July 2005 following a trial.
He suffered a hamstring injury in August and a shoulder injury in September. He joined Conference North team Stalybridge Celtic on loan on 17 March 2006 and played in nine games during the 2005-2006 season.
He was released by York in May after failing to feature in the first team He signed for Stalybridge permanently on 7 July and he finished the 2006-2007 season with 40 appearances and five goals.
He decided to leave the club at the end of the season, but in August eventually signed a new contract.
He played for Stalybridge in the 2008 Conference North play-off Final, which the team lost 1–0 to Barrow, and he finished the season with 2007-2008 with 35 appearances and eight goals. He joined newly promoted Conference National side Barrow in July 2008. After failing to secure a regular place, however, he joined Southport on a month"s loan on 5 December, with a view to a permanent transfer.
He made his debut a day later in a 1–0 defeat at AFC Telford United and his first goals came after scoring twice in a 5–2 victory over Gainsborough Trinity on 20 December.
A permanent move to Southport took place on 21 January 2009 after he was signed for a fee of £2,500. He played for Southport in their 2–1 defeat on aggregate to Gateshead in the Conference North play-off semi-final and he finished the 2008-2009 season with 29 appearances and three goals for Southport.
Winn signed for Gateshead on 1 November 2010, initially on loan with a fee of £2,500 agreed for a permanent transfer in January 2011. He scored his first goal for the club on 5 March 2011 in a 1–1 draw with Altrincham at Moss Lane.
Winn was made available for transfer by Gateshead on 4 May 2011, and after a successful trial, signed for Farnborough on 10 July 2011 on a free transfer.