Football League Cup 1997/98, First Round |
 | 12.08.1997 |  | Port Vale | – | York City | | 1:2 (1:1) |
| Stoke-on-Trent |
Football League Cup 1996/97, Second round |
| 24.09.1996 | | York City | – | Everton | | 3:2 (1:1) |
| York |
Football League Cup 1996/97, First Round |
| 03.09.1996 | | York City | – | Doncaster Rovers | | 2:0 (1:0) |
| York |
Football League Cup 1995/96, Second round |
| 20.09.1995 | | Manchester United | – | York City | | 0:3 (0:1) |
| Manchester |
Football League Cup 1995/96, First Round |
| 22.08.1995 | | York City | – | Rochdale | | 5:1 aet |
| York |
Football League Cup 1989/90, First Round |
| 29.08.1989 | | York City | – | Hartlepool United | | 4:1 |
| York |
Football League Cup 1987/88, First Round |
| 25.08.1987 | | York City | – | Halifax Town | | 1:0 aet
(0:0) |
| York |
Football League Cup 1986/87, Second round |
| 23.09.1986 | | York City | – | Chelsea | | 1:0 |
| York |
Football League Cup 1986/87, First Round |
| 26.08.1986 | | Sunderland | – | York City | | 2:4 |
| Sunderland |
Football League Cup 1985/86, First Round |
| 04.09.1985 | | Lincoln City | – | York City | | 1:2 |
| |
Football League Cup 1985/86, First Round |
| 20.08.1985 | | York City | – | Lincoln City | | 2:1 |
| |
Football League Cup 1984/85, First Round |
| 04.09.1984 | | York City | – | Doncaster Rovers | | 5:0 |
| |
Football League Cup 1984/85, First Round |
| 28.08.1984 | | Doncaster Rovers | – | York City | | 2:3 |
| |
Football League Cup 1982/83, First Round |
| 31.08.1982 | | York City | – | Lincoln City | | 2:1 |
| |
Football League Cup 1980/81, Second round |
| 27.08.1980 | | York City | – | Bristol Rovers | | 2:1 |
| |
Football League Cup 1980/81, First Round |
| 09.08.1980 | | York City | – | Hartlepool United | | 2:1 |
| |
Football League Cup 1979/80, First Round |
| 14.08.1979 | | York City | – | Mansfield Town | | 3:2 aet |
| |
Football League Cup 1977/78, First Round |
| 16.08.1977 | | York City | – | Rotherham United | | 3:0 |
| |
Football League Cup 1975/76, First Round |
| 26.08.1975 | | York City | – | Bradford City | | 3:0 |
| |
Football League Cup 1973/74, Third round |
| 06.11.1973 | | York City | – | Orient | | 2:1 * |
| |
Football League Cup 1973/74, Second round |
| 09.10.1973 | | York City | – | Aston Villa | | 1:0 (0:0) |
| York |
Football League Cup 1973/74, First Round |
| 29.08.1973 | | York City | – | Huddersfield Town | | 1:0 |
| |
Football League Cup 1971/72, Second round |
| 14.09.1971 | | Middlesbrough | – | York City | | 1:2 * |
| |
Football League Cup 1971/72, First Round |
| 18.08.1971 | | Darlington | – | York City | | 0:1 |
| |
Football League Cup 1970/71, First Round |
| 19.08.1970 | | Hartlepool | – | York City | | 2:3 |
| |
Football League Cup 1966/67, Second round |
| 13.09.1966 | | York City | – | Chesterfield | | 3:2 |
| |
Football League Cup 1966/67, First Round |
| 29.08.1966 | | York City | – | Middlesbrough | | 2:1 * |
| |
Football League Cup 1965/66, First Round |
| 07.09.1965 | | York City | – | Lincoln City | | 4:2 * |
| |
Football League Cup 1963/64, First Round |
| 23.09.1963 | | York City | – | Doncaster Rovers | | 3:0 * |
| |
Football League Cup 1961/62, Fourth Round |
| 13.12.1961 | | York City | – | Bournemouth & Boscombe Athletic | | 1:0 |
| |
Football League Cup 1961/62, Third round |
| 04.12.1961 | | York City | – | Watford | | 3:2 * |
| |
Football League Cup 1961/62, Second round |
| 09.10.1961 | | York City | – | Leicester City | | 2:1 |
| |
Football League Cup 1961/62, First Round |
| 13.09.1961 | | York City | – | Bristol City | | 3:0 |
| |
