Cleethorpes also reached the FA Vase final that season, losing 4–0 to South Shields in the final at Wembley Stadium on 21 May 2017, with Winn playing the whole match. He spent three years at Cleethorpes before joining Northern Counties East Division One club Grimsby Borough in July 2018. Winn made his Grimsby Borough debut in a 0–0 draw at home to Shirebrook Town on 4 August 2018, before scoring his first goal for the club four days later in a 10–0 victory against FC Bolsover. The club won the Division One title in Winn's first year with the club, leapfrogging league leaders Campion by beating them 4–2 on the final day of the season. He made 33 appearances during the season, scoring four times. Winn signed for divisional rivals Barton Town on 5 July 2019. He made his Barton debut in the club's first victory of the 2019–20 season, playing the whole match in a 3–2 win over Carlton Town in the FA Cup extra preliminary round on 10 August 2019. Winn has predominantly been deployed as a winger throughout his career. He has adapted to play as a full-back for both Cleethorpes Town and Grimsby Borough in recent seasons. Stevenage  Cleethorpes Town  Grimsby Borough