| Season | Date | Opponent | Round | Replay | H/A | Score | Ground | Notes |
|---|
| 1878-79 | Sat Mar 22, 1879 | Old Etonians | Semi | | N | 1-2 | Kennington Oval | |
| 1879-80 | Sat Mar 27, 1880 | Oxford University | Semi | | N | 0-1 | Kennington Oval | |
| 1884-85 | Sat Mar 14, 1885 | Queen's Park | Semi | | N | 1-1 | Derby Cricket Ground | |
| Sat Mar 28, 1885 | Queen's Park | Semi | Rep 1 | N | 0-3 | Merchiston Castle School | |
| 1891-92 | Sat Feb 27, 1892 | West Bromwich Albion | Semi | | N | 1-1 | Molineux | |
| Sat Mar 05, 1892 | West Bromwich Albion | Semi | Rep 1 | N | 1-1 | Molineux | |
| Wed Mar 09, 1892 | West Bromwich Albion | Semi | Rep 2 | N | 2-6 | Baseball Ground | |
| 1897-98 | Sat Mar 19, 1898 | Southampton St Mary's | Semi | | N | 1-1 | Bramall Lane | Played at Sheffield United |
| Thu Mar 24, 1898 | Southampton St Mary's | Semi | Rep 1 | N | 2-0 | Crystal Palace | Played at Crystal Palace |
| 1899-00 | Sat Mar 24, 1900 | Bury | Semi | | N | 1-1 | Victoria Ground | |
| Thu Mar 29, 1900 | Bury | Semi | Rep 1 | N | 2-3 | Bramall Lane | |
| 1901-02 | Sat Mar 15, 1902 | Southampton | Semi | | N | 1-3 | White Hart Lane | Played at Tottenham Hotspur |
| 1958-59 | Sat Mar 14, 1959 | Aston Villa | Semi | | N | 1-0 | Hillsborough | Played at Sheffield Wednesday |
| 1966-67 | Sat Apr 29, 1967 | Tottenham Hotspur | Semi | | N | 1-2 | Hillsborough | Played at Sheffield Wednesday |
| 1987-88 | Sat Apr 09, 1988 | Liverpool | Semi | | N | 1-2 | Hillsborough | Played at Sheffield Wednesday |
| 1988-89 | Sat Apr 15, 1989 | Liverpool | Semi | | N | 0-0 | Hillsborough | Abandoned due to Hillsborough Disaster |
| Sun May 07, 1989 | Liverpool | Semi | Rep 1 | N | 1-3 | Old Trafford | Played at Manchester United |
| 1990-91 | Sun Apr 14, 1991 | West Ham United | Semi | | N | 4-0 | Villa Park | Played at Aston Villa |
| 2024-25 | Sun Apr 27, 2025 | Manchester City | Semi | | N | - | Wembley (New) | |
