Football League Cup 2015/16, First Round |
 | 11.08.2015 |  | York City | – | Bradford City | | 2:2 aet
(0:1, 2:2),
pen. 4:2 |
| York |
Football League Cup 2012/13, First Round |
| 11.08.2012 | | Doncaster Rovers | – | York City | | 1:1 aet
(0:0, 1:1),
pen. 4:2 |
| Doncaster |
Football League Cup 2001/02, First Round |
| 21.08.2001 | | York City | – | Crewe Alexandra | | 2:2 aet
(1:1, 1:1),
pen. 5:6 |
| York |
Football League Cup 2000/01, First Round |
| 06.09.2000 | | Stoke City | – | York City | | 0:0 |
| Stoke-on-Trent |
Football League Cup 1997/98, First Round |
| 26.08.1997 | | York City | – | Port Vale | | 1:1 (1:0) |
| York |
Football League Cup 1996/97, Second round |
| 18.09.1996 | | Everton | – | York City | | 1:1 (0:0) |
| Liverpool |
Football League Cup 1996/97, First Round |
| 20.08.1996 | | Doncaster Rovers | – | York City | | 1:1 (1:1) |
| Doncaster |
Football League Cup 1994/95, First Round |
| 23.08.1994 | | York City | – | Burnley | | 2:2 (1:0) |
| York |
Football League Cup 1993/94, First Round |
| 24.08.1993 | | York City | – | Rochdale | | 0:0 |
| York |
Football League Cup 1992/93, First Round |
| 25.08.1992 | | York City | – | Chesterfield | | 0:0 |
| York |
Football League Cup 1991/92, First Round |
| 20.08.1991 | | Bolton Wanderers | – | York City | | 2:2 (1:0) |
| Bolton |
Football League Cup 1989/90, First Round |
| 23.08.1989 | | Hartlepool United | – | York City | | 3:3 |
| Hartlepool |
Football League Cup 1988/89, First Round |
| 30.08.1988 | | York City | – | Sunderland | | 0:0 |
| York |
Football League Cup 1987/88, Second round |
| 23.09.1987 | | Leeds United | – | York City | | 1:1 |
| Leeds |
Football League Cup 1987/88, First Round |
| 18.08.1987 | | Halifax Town | – | York City | | 1:1 |
| Halifax |
Football League Cup 1985/86, Second round |
| 24.09.1985 | | Grimsby Town | – | York City | | 1:1 |
| |
Football League Cup 1981/82, First Round |
| 15.09.1981 | | York City | – | Sheffield United | | 1:1 |
| |
Football League Cup 1980/81, First Round |
| 12.08.1980 | | Hartlepool United | – | York City | | 0:0 |
| |
Football League Cup 1977/78, First Round |
| 23.08.1977 | | York City | – | Rotherham United | | 1:1 aet,
pen. 5:6 * |
| |
Football League Cup 1976/77, First Round |
| 17.08.1976 | | Barnsley | – | York City | | 0:0 |
| |
Football League Cup 1976/77, First Round |
| 14.08.1976 | | York City | – | Barnsley | | 0:0 |
| |
Football League Cup 1973/74, Fourth Round |
| 21.11.1973 | | York City | – | Manchester City | | 0:0 |
| |
Football League Cup 1973/74, Third round |
| 31.10.1973 | | Orient | – | York City | | 1:1 |
| |
Football League Cup 1971/72, Second round |
| 08.09.1971 | | York City | – | Middlesbrough | | 2:2 |
| |
Football League Cup 1970/71, Second round |
| 15.09.1970 | | Northampton Town | – | York City | | 1:1 aet * |
| |
Football League Cup 1970/71, Second round |
| 09.09.1970 | | York City | – | Northampton Town | | 0:0 |
| |
Football League Cup 1966/67, First Round |
| 24.08.1966 | | Middlesbrough | – | York City | | 0:0 |
| |
Football League Cup 1965/66, First Round |
| 01.09.1965 | | Luton Town | – | York City | | 2:2 |
| |
Football League Cup 1963/64, Second round |
| 25.09.1963 | | York City | – | Lincoln City | | 1:1 |
| |
Football League Cup 1963/64, First Round |
| 04.09.1963 | | Doncaster Rovers | – | York City | | 0:0 |
| |
Football League Cup 1962/63, First Round |
| 05.09.1962 | | York City | – | Lincoln City | | 2:2 |
| |
Football League Cup 1961/62, Third round |
| 21.11.1961 | | Watford | – | York City | | 2:2 aet * |
| |
Football League Cup 1961/62, Third round |
| 15.11.1961 | | York City | – | Watford | | 1:1 |
| |
