For the 1924–25 season, the Midland League was reorganised because eight Football League clubs withdrew their reserve teams from the competition. York finished sixth in the Principal Competition that concluded in February 1925 and were runners-up to Denaby United in the North Subsidiary Competition. The club struggled financially in this period, and was only kept going by the enthusiasm and generosity of the directors. John Fisher, one of these benefactors, was elected chairman in 1925. The Midland League was restored to its previous size for 1925–26 and York finished in 16th place after a poor start to the season, from which they never recovered. York enjoyed their most successful Midland League season in 1926–27, when they finished in sixth place and scored 96 goals in 38 league matches. They surpassed the FA Cup's qualifying rounds for the first time this season, being beaten 2–1 by Second Division team Grimsby Town at Blundell Park in the second round. In 1927, the club made its first serious attempt for election to the Football League, but Barrow and Accrington Stanley were re-elected instead. Fisher resigned as chairman in August and Brown took the position for the second time. After ranking seventh in the Midland League in the 1927–28 season, York appointed their first official manager in July 1928, with Jock Collier named as player-manager. York finished ninth in the 1928–29 season, and Jimmy Cowie was the divisional top scorer with 49 goals. This was York's last season in the Midland League as the club won election to the Football League on 3 June 1929, taking the place of Ashington in the Third Division North.
