During the 2016–17 season, Winn helped the club to Northern Counties East Premier Division and Lincolnshire Senior Trophy titles, whilst also finishing runner-up in the FA Vase.
After three years at Cleethorpes, Winn joined Grimsby Borough of Northern Counties East Division One in July 2018, with the club winning the league title during his one season there.
Winn began his career in the youth system at Scunthorpe United,[3] and was named as the club's Young Player of the Year for the 2006–07 season.
[5] He made his debut for Scunthorpe at the age of 17 while a second-year scholar at the club, starting in a 2–1 victory over Bradford City in the Football League Trophy in October 2006.
[6] He also made an appearance as a second-half substitute in the same competition in the next round against Port Vale, with Scunthorpe losing the tie 5–3 on a penalty shoot-out, drawing 0–0 after extra-time.
[8] During the early stages of the 2008–09 season, Mansfield Town registered transfer interest in Winn, hoping to sign him on loan.
[4][10][11] He had a trial at York City in February, playing in a reserve team game against Grimsby Town, although no transfer materialised.
[12] Winn joined Barrow on an emergency one-month loan in February 2009, where he played three times before returning to his parent club.
[25] On his move to the club, Winn stated "it's a good feeling having signed for Stevenage as I wanted to play in the Football League again next season and I've now got the chance".
[42] No transfer to Cambridge materialised, and, in March 2012, Winn joined Conference Premier club Grimsby Town on loan until the end of the 2011–12 season, where he made 10 appearances.
[45] A month after being released by Stevenage, Winn signed for Conference Premier club Macclesfield Town on a free transfer.
[50] He remained at Macclesfield for the 2013–14 season, scoring his only goal for the club in a 4–0 victory over League One opponents Swindon Town in the FA Cup on 9 November 2013.
[58] He was recalled by his parent club on 8 April 2015,[58] and ended the season by coming on as a substitute in Chester's final two league matches,[54] both of which were victories.
[63] Winn made his Grimsby Borough debut in a 0–0 draw at home to Shirebrook Town on 4 August 2018,[64] before scoring his first goal for the club four days later in a 10–0 victory against FC Bolsover.
[67] He made his Barton debut in the club's first victory of the 2019–20 season,[68] playing the whole match in a 3–2 win over Carlton Town in the FA Cup extra preliminary round on 10 August 2019.