| 1886 | FA Cup | West Bromwich Albion | Stoney Lane | L | 1-3 |
| 1892 | Football League | Stoke | Molineux | W | 4-1 |
| 1893 | Football League | Sunderland | Newcastle Road | L | 2-5 |
| 1897 | Football League | Blackburn Rovers | Ewood Park | L | 0-2 |
| 1904 | Football League | Derby County | Molineux | D | 2-2 |
| 1909 | Football League | Blackpool | Bloomfield Road | L | 1-3 |
| 1915 | Football League | Arsenal | Highbury | L | 1-5 |
| 1926 | Football League | Preston North End | Deepdale | L | 0-1 |
| 1932 | Football League | Tottenham Hospur | White Hart Lane | D | 3-3 |
| 1937 | Football League | Sheffield Wednesday | Hillsborough | W | 3-1 |
| 1943 | War Competition | Aston Villa | Molineux | L | 0-4 |
| 1954 | Football League | Cardiff City | Ninian Park | W | 3-1 |
| 1956 | Football League | Sunderland | Roker Park | D | 1-1 |
| 1960 | Football League | Arsenal | Highbury | D | 4-4 |
| 1965 | Football League | Arsenal | Highbury | L | 1-4 |
| 1971 | FA Cup | Norwich City | Molineux | W | 5-1 |
| 1978 | Football League | Bristol City | Molineux | D | 0-0 |
| 1982 | FA Cup | Leeds United | Molineux | L | 1-3 |
| 1984 | Football League | Queens Park Rangers | Loftus Road | L | 1-2 |
| 1988 | Football League | Crewe Alexandra | Gresty Road | W | 2-0 |
| 1989 | Football League | Chester City | Molineux | W | 3-1 |
| 1993 | FA Cup | Watford | Vicarage Road | W | 4-1 |
| 1995 | Football League | Sheffield United | Molineux | D | 2-2 |
| 1999 | FA Cup | Bolton Wanderers | Reebok Stadium | W | 2-1 |
| 2006 | Football League | Coventry City | Ricoh Arena | L | 0-2 |
| 2012 | Premier League | Chelsea | Molineux | L | 1-2 |
| 2017 | Football League | Sheffield Wednesday | Hillsborough | D | 0-0 |
| 2018 | Football League | Brentford | Molineux | W | 3-0 |
| 2019 | Premier League | Crystal Palace | Molineux | L | 0-2 |
| 2021 | Premier League | Brighton & Hove Albion | AMEX Stadium | D | 3-3 |
