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.

[17] 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 2007–08 with 35 appearances and eight goals.

[19] 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.

[20] 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.

[21] He made 34 appearances and scored one goal for Southport as they won the Conference North title in the 2009–10 season, having been converted successfully from his regular central position into a right sided winger by manager Liam Watson.