of the 2017 season with Oldham Athletic. Cheltenham Town Winchester signed for Cheltenham Town on 12 January 2017 on a free transfer. Winchester made his debut for Cheltenham Town on 14 January 2017 in a 3–0 home win against Accrington Stanley. He was substituted in the eighty-first minute for Kyle Storer. Forest Green Rovers In May 2018, Winchester signed for Gloucestershire rivals Forest Green Rovers on a two-year contract. Sunderland On 10 January 2021, Winchester signed for Sunderland on an initial two and a half year deal for an undisclosed fee. He was cup-tied for Sunderland's victory in the 2021 EFL Trophy Final. International career Already a Northern Irish under-16s international, he made his under-17s international debut on 17 March 2010 in the UEFA Under-17s Championship elite round match against Spain, followed up by matches against Poland and Belgium later that week. In August 2010 he was called up to the under-18s team and played all three matches for them in an international tournament in Poland. In February 2011, Winchester was called up to the Northern Ireland under-21s team Winchester earned his first cap for the Northern Ireland U-21s against Wales U-21 on 9 February 2011 aged just 17. In March 2011 he was called up for the Northern Ireland under-19s team for the first time. He made his debut at under-19s level on 11 April in a friendly against Slovakia, scoring one of the three Northern Irish goals in the match, his first goal for his country. On 13 May 2011 he was again called up to the Northern Ireland under-21s as a squad member against Faroe Islands in a Euro qualifier on 31 May. Seven days later he received his first call up to the senior Northern Ireland national football team for the Celtic Cup matches against Republic of Ireland and Wales on 24 and 27 May. In the Republic of Ireland match he was an unused substitute as Northern Ireland lost 5–0 before making his debut as a substitute for the full international team on 27 May against Wales. In June 2011 he received his first call-up to the Northern Ireland under-20s team, alongside teammate Kirk Millar for July's Milk Cup tournament. In September 2011, Winchester was called up to the Northern Ireland under-21s for the European Championship qualifiers against Serbia U-21s and Denmark U-21s, Winchester was an unused substitute against Serbia U-21s in a 1–0 defeat.