Following the expiry of his loan at the end of the season, Colchester expressed an interest in signing Wynter on a permanent basis, but a move did not come to fruition, despite stating himself that he would be happy to return should the opportunity arise. Portsmouth loan Wynter joined League Two Portsmouth in a season-long loan deal in July 2014. He made his debut in Portsmouth's 1–0 win over League One opposition Peterborough United in the League Cup on 12 August, and played in Pompey's 3–1 Football League Trophy triumph over Yeovil Town on 2 September, but didn't make his first league appearance until 7 September, starting in their 2–0 away defeat to Burton Albion. Wynter was played in a wing-back role by Portsmouth manager Andy Awford, despite never having played in the position before, and said that he was "ready to thrive" in his new position. Following a string of poor performances, Awford scrapped his 3-5-2 system that utilised wing-backs, but did not blame Wynter or his teammates for the lack of function within the system. After making 15 appearances for Portsmouth in all competitions, Awford brought in Gillingham loanee Matt Fish as a replacement for Wynter, but insisted he would remain a part of his squad but the situation would be reassessed in the January transfer window. However, on 28 December, both Fish and Wynter returned to their parent clubs after the loans were not renewed with both players having fallen out of favour at Fratton Park. Colchester United Wynter rejoined Colchester United on 10 January 2015, on this occasion on a permanent basis, signing an 18-month contract ahead of the U's League One game against Peterborough United the same day. He made his second debut for the club later that day, starting in defence and helping his teammates to a clean sheet in a 2–0 victory at London Road. During Colchester's FA Cup fourth round match against Tottenham Hotspur on 30 January 2016, Wynter was involved in a sickening collision with fellow U's defender Tom Eastman after just two minutes of the game. Wynter suffered concussion and a seizure while on the field. He was taken to hospital, where he was reported to have been sitting up and talking by half-time in the 4–1 defeat for Colchester. He finally made a return to first-team action on 23 April when he came on for Gavin Massey in a