Winn made his debut for Cambridge in a 1–0 away win at Newport County on 3 September 2011, playing 71 minutes of the match. He went on to make 13 appearances for the club, scoring once in a 2–0 home victory against Ebbsfleet United on 20 September 2011. Winn returned to Stevenage when his 93-day loan deal expired on 1 December 2011, with Cambridge manager Jez George stating the club would consider a permanent transfer in the 2012 January transfer window.
Winn entered the scene for Cambridge in a 1–0 road victory over Newport County on 3 September 2011, playing 71 minutes of the game. He went on to make 13 appearances for the team, scoring once in a 2–0 home win against Ebbsfleet United on 20 September 2011. Winn returned to Stevenage when his 93-day loan period concluded on 1 December 2011, with Cambridge manager Jez George indicating that the club would explore a permanent transfer in the January 2012 transfer window.