[3] In the same year, York reached the final of the North Riding Senior Cup, but lost 4–2 to Middlesbrough reserves at Ayresome Park on 10 March.
[6] The club's first season proved disappointing financially, with a loss of £718 reported, and as a consequence Shaw relinquished the chairmanship to Arthur Brown.
[11] After ranking seventh in the Midland League in the 1927–28 season,[5] York appointed their first official manager in July 1928, with Jock Collier named as player-manager.
[17] Reg Stockill, the scorer of the first goal, became the youngest player to represent the club in a competitive match at the age of 15 years and 281 days.
[20] Sherrington's first season in charge saw York rank 12th in the league,[21] and they again faced First Division opposition in the FA Cup third round, taking Sheffield United to a replay.
[23] In August 1932, York moved to a new ground at Bootham Crescent,[24] which was closer than Fulfordgate to the club's centre of support and the railway station.
[29] The club finished in 15th place in the 1934–35 season,[30] and Bootham Crescent staged its first match against First Division opposition when Derby County defeated York 1–0 in the FA Cup third round.
[38] By the end of that season's FA Cup run, York were on the fringe of the promotion race, but faltered in the closing weeks[39] and finished in 11th place.
[54] In the 1943–44 Football League North, the team finished 31st of 50 clubs,[55] and after qualifying for the War Cup knock-out stages were eliminated 7–2 over two legs by Bradford Park Avenue in the second round.
[73] York were forced to apply for re-election to retain their place in the Football League for the first time,[74] after finishing bottom of the Third Division North in the 1949–50 season.
[74] York's fortunes improved in 1950–51; they ranked 17th in the league[76] and reached the FA Cup third round for the first time since 1946, when they were beaten 2–0 by First Division team Bolton Wanderers at Burnden Park.
[80] Sheffield United's assistant manager Jimmy McCormick was appointed in June,[81] and by late December York were bottom of the table.
[87] York beat Scarborough, Dorchester Town, Blackpool (winners of the competition 18 months earlier), Bishop Auckland, Tottenham Hotspur and Notts County in the previous rounds before playing Newcastle United in the semi-final.
[88] After drawing 1–1 at Hillsborough, York were defeated 2–0 in the replay at Roker Park, which ended an FA Cup campaign in which Arthur Bottom scored eight goals.
[91] By the end of the cup run, York were on the fringes of the Third Division North promotion race, but injuries and a congested fixture list led to them finishing fourth in the 1954–55 season.
[97] That season's FA Cup run included a 2–1 win over a Swansea Town team featuring eight Wales internationals at Vetch Field in the third round.
[98] They then played First Division team Sunderland, billed as the "Bank of England club" because of their high expenditure on transfers, York were beaten 2–1 at Roker Park in a replay.
[95] During this season, York filled the managerial position that had been vacant for the last 18 months; Arsenal player Don Roper rejected the job before Sam Bartram was appointed in March 1956.
[102] York led the Fourth Division until early November 1958,[103] and despite faltering midseason continued strongly to finish third in 1958–59 and gain promotion for the first time.
[19] In this competition, they beat First Division team Leicester City, but were eliminated after a 2–1 defeat to divisional rivals Rochdale at Spotland Stadium in the fifth round.
[119] During this season, a match-fixing scandal exposed by the newspaper Sunday People accused York player Jack Fountain of fixing match results.
[126] Shaw resigned for personal reasons a week into the 1968–69 season, and former Huddersfield Town manager Tom Johnston succeeded him in October.
[132] York reached the fourth round of the FA Cup for the first time since 1958, and played two Second Division teams; after beating Cardiff City 3–1 at St Andrew's in a second replay, they lost 4–1 to Middlesbrough at Ayresome Park.
[134] They also reached the FA Cup fourth round for the second successive season; after drawing 3–3 at home to First Division team Southampton they were beaten 3–2 in the replay at the Dell.
[137] Another downturn in form followed before York beat Rotherham United in the last match of the season[137] to finish 18th, avoiding relegation from the Third Division on goal average for the second successive year.
[141] This season, York held First Division team Manchester City to a 0–0 home draw in the League Cup fourth round, before being beaten 4–1 in the replay at Maine Road.
[143] Johnston left to take over at Huddersfield Town in January 1975,[146] and was succeeded in February by former Manchester United manager Wilf McGuinness.
[150] The midseason signings Chris Galvin and Gordon Staniforth marked an improvement in results,[151] but after winning only 1 of their last 15 matches[150] they finished in bottom place and were relegated for the second successive season.
[155] York remained in the lower reaches of the table[153] and finished the season in 22nd place,[156] forcing the club to apply for re-election for the sixth time.
[151] This season, attendances fell to an all-time low, and amid growing financial trouble, Michael Sinclair took over as chairman in April 1978 in a boardroom shuffle.