Football League Cup 2015/16, Second round |
 | 25.08.2015 |  | Swansea City | – | York City |  | 3:0 (1:0) |
| Swansea |
Football League Cup 2014/15, First Round |
| 12.08.2014 | | York City | – | Doncaster Rovers | | 0:1 (0:0) |
| York |
Football League Cup 2013/14, First Round |
| 06.08.2013 | | York City | – | Burnley | | 0:4 (0:1) |
| York |
Football League Cup 2003/04, First Round |
| 12.08.2003 | | Rotherham United | – | York City | | 2:1 (2:1) |
| Rotherham |
Football League Cup 2002/03, First Round |
| 10.09.2002 | | Sheffield United | – | York City | | 1:0 (1:0) |
| Sheffield |
Football League Cup 2000/01, First Round |
| 22.08.2000 | | York City | – | Stoke City | | 1:5 (0:1) |
| York |
Football League Cup 1999/00, First Round |
| 24.08.1999 | | Wigan Athletic | – | York City | | 2:1 (1:0) |
| Wigan |
Football League Cup 1999/00, First Round |
| 10.08.1999 | | York City | – | Wigan Athletic | | 0:1 (0:0) |
| York |
Football League Cup 1998/99, First Round |
| 18.08.1998 | | Sunderland | – | York City | | 2:1 (0:0) |
| Sunderland |
Football League Cup 1998/99, First Round |
| 11.08.1998 | | York City | – | Sunderland | | 0:2 (0:2) |
| York |
Football League Cup 1997/98, Second round |
| 23.09.1997 | | York City | – | Oxford United | | 1:2 (0:0) |
| York |
Football League Cup 1997/98, Second round |
| 16.09.1997 | | Oxford United | – | York City | | 4:1 (0:1) |
| Oxford |
Football League Cup 1996/97, Third round |
| 22.10.1996 | | York City | – | Leicester City | | 0:2 (0:0) |
| York |
Football League Cup 1995/96, Third round |
| 25.10.1995 | | Queens Park Rangers | – | York City | | 3:1 (1:1) |
| London |
Football League Cup 1995/96, Second round |
| 03.10.1995 | | York City | – | Manchester United | | 1:3 (1:2) |
| York |
Football League Cup 1995/96, First Round |
| 15.08.1995 | | Rochdale | – | York City | | 2:1 (1:0) |
| Rochdale |
Football League Cup 1994/95, First Round |
| 18.08.1994 | | Burnley | – | York City | | 1:0 (0:0) |
| Burnley |
Football League Cup 1993/94, First Round |
| 17.08.1993 | | Rochdale | – | York City | | 2:0 (0:0) |
| Rochdale |
Football League Cup 1992/93, First Round |
| 18.08.1992 | | Chesterfield | – | York City | | 2:0 (0:0) |
| Chesterfield |
Football League Cup 1991/92, First Round |
| 27.08.1991 | | York City | – | Bolton Wanderers | | 1:2 (1:1) |
| York |
Football League Cup 1990/91, First Round |
| 04.09.1990 | | Wrexham | – | York City | | 2:0 |
| Wrexham |
Football League Cup 1990/91, First Round |
| 28.08.1990 | | York City | – | Wrexham | | 0:1 |
| York |
Football League Cup 1989/90, Second round |
| 03.10.1989 | | Southampton | – | York City | | 2:0 |
| Southampton |
Football League Cup 1989/90, Second round |
| 20.09.1989 | | York City | – | Southampton | | 0:1 |
| York |
Football League Cup 1988/89, First Round |
| 06.09.1988 | | Sunderland | – | York City | | 4:0 |
| Sunderland |
Football League Cup 1987/88, Second round |
| 06.10.1987 | | York City | – | Leeds United | | 0:4 |
| York |
Football League Cup 1986/87, Second round |
| 08.10.1986 | | Chelsea | – | York City | | 3:0 |
| London |
Football League Cup 1986/87, First Round |
| 02.09.1986 | | York City | – | Sunderland | | 1:3 aet |
| York |
Football League Cup 1985/86, Second round |
| 08.10.1985 | | York City | – | Grimsby Town | | 2:3 |
| |
Football League Cup 1984/85, Second round |
| 09.10.1984 | | Queens Park Rangers | – | York City | | 4:1 |
| |
Football League Cup 1984/85, Second round |
| 25.09.1984 | | York City | – | Queens Park Rangers | | 2:4 |
| |
Football League Cup 1983/84, First Round |
| 13.09.1983 | | Grimsby Town | – | York City | | 2:0 aet |
| |
Football League Cup 1982/83, First Round |
| 15.09.1982 | | Lincoln City | – | York City | | 3:1 |
| |
Football League Cup 1981/82, First Round |
| 01.09.1981 | | Sheffield United | – | York City | | 1:0 |
| |
Football League Cup 1980/81, Second round |
| 03.09.1980 | | Bristol Rovers | – | York City | | 1:0 aet |
| |
Football League Cup 1979/80, First Round |
| 11.08.1979 | | Mansfield Town | – | York City | | 1:0 |
| |
Football League Cup 1978/79, First Round |
| 15.08.1978 | | York City | – | Grimsby Town | | 0:3 |
| |
Football League Cup 1978/79, First Round |
| 12.08.1978 | | Grimsby Town | – | York City | | 2:0 |
| |
Football League Cup 1977/78, First Round |
| 13.08.1977 | | Rotherham United | – | York City | | 3:0 |
| |
Football League Cup 1976/77, First Round |
| 24.08.1976 | | York City | – | Barnsley | | 1:2 aet * |
| |
Football League Cup 1975/76, Second round |
| 10.09.1975 | | York City | – | Liverpool | | 0:1 |
| |
Football League Cup 1975/76, First Round |
| 20.08.1975 | | Bradford City | – | York City | | 2:0 |
| |
Football League Cup 1974/75, First Round |
| 21.08.1974 | | York City | – | Huddersfield Town | | 0:2 |
| |
Football League Cup 1973/74, Fourth Round |
| 05.12.1973 | | Manchester City | – | York City | | 4:1 * |
| Manchester |
Football League Cup 1972/73, First Round |
| 16.08.1972 | | Notts County | – | York City | | 3:1 |
| |
Football League Cup 1971/72, Third round |
| 05.10.1971 | | Sheffield United | – | York City | | 3:2 |
| |
Football League Cup 1970/71, Second round |
| 28.09.1970 | | York City | – | Northampton Town | | 1:2 * |
| |
Football League Cup 1969/70, First Round |
| 13.08.1969 | | Darlington | – | York City | | 3:0 |
| |
Football League Cup 1968/69, First Round |
| 14.08.1968 | | York City | – | Barnsley | | 3:4 |
| |
Football League Cup 1967/68, First Round |
| 23.08.1967 | | Darlington | – | York City | | 1:0 |
| |
Football League Cup 1966/67, Third round |
| 04.10.1966 | | York City | – | Blackburn Rovers | | 0:2 |
| |
Football League Cup 1965/66, Second round |
| 22.09.1965 | | Millwall | – | York City | | 4:1 |
| |
Football League Cup 1964/65, First Round |
| 02.09.1964 | | Bradford City | – | York City | | 2:0 |
| |
Football League Cup 1963/64, Second round |
| 14.10.1963 | | Lincoln City | – | York City | | 2:0 * |
| |
Football League Cup 1962/63, First Round |
| 19.09.1962 | | Lincoln City | – | York City | | 2:0 * |
| |
Football League Cup 1961/62, Fifth Round |
| 07.02.1962 | | Rochdale | – | York City | | 2:1 |
| |
Football League Cup 1960/61, First Round |
| 10.10.1960 | | York City | – | Blackburn Rovers | | 1:3 |
| |
