The 1995–96 season saw Cinderford reach the first round of the FA Cup for the first time. After beating Bromsgrove Rovers 2–1, they lost 3–0 at Gravesend & Northfleet in a second round replay. The club were transferred to the Division One Midlands in 1998, and back to the renamed Division One Western in 1999. In 2000–01 the club won the Gloucestershire Senior Cup, beating Bristol City 1–0 in the final. They were moved back to the Division One Midlands in 2006, before returning to Division One South & West in two years later. In 2015–16 they won the division and were promoted to the Premier Division. The club initially tried to refuse promotion due to concerns about increased costs, but this was rejected by the Football Association.