| First Team Matches | Second Team Matches | Youth Team Matches | League debuts | Associated with both clubs | Transfers |
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| Season | Competition | Date | Venue | Result | ||
| 1906/07 | Football League | 15 December 1906 | Molineux | W | 2-1 | As Chesterfield Town |
| 1906/07 | Football League | 20 April 1907 | Recreation Ground | L | 2-3 | |
| 1907/08 | Football League | 23 November 1907 | Molineux | D | 0-0 | |
| 1907/08 | Football League | 21 March 1908 | Recreation Ground | L | 0-2 | |
| 1908/09 | Football League | 12 September 1908 | Recreation Ground | D | 1-1 | |
| 1908/09 | Football League | 9 January 1909 | Molineux | W | 3-0 | |
| 1923/24 | Football League | 25 August 1923 | Recreation Ground | D | 0-0 | As Chesterfield |
| 1923/24 | Football League | 1 September 1923 | Molineux | W | 2-1 | |
| 1931/32 | Football League | 12 September 1931 | Molineux | W | 6-0 | |
| 1931/32 | Football League | 27 January 1932 | Recreation Ground | W | 2-1 | |
| 1948/49 | FA Cup | 8 January 1949 | Molineux | W | 6-0 | |
| 1981/82 | Friendly | 10 August 1981 | Castlecroft | Unknown | Behind Closed Doors | |
| 1985/86 | Football League | 1 January 1986 | Molineux | W | 1-0 | |
| 1985/86 | Football League | 29 March 1986 | Recreation Ground | L | 0-3 | |
| 1988/89 | Football League | 10 September 1988 | Recreation Ground | W | 3-0 | |
| 1988/89 | Football League | 21 January 1989 | Molineux | W | 1-0 | |
| 1994/95 | FL Cup | 20 September 1994 | Molineux | W | 1-0 | |
| 1994/95 | FL Cup | 27 September 1994 | Recreation Ground | W | 3-1 | |
| 2006/07 | FL Cup | 23 August 2006 | Recreation Ground | D | 0-0* | |
| 2013/14 | Friendly | 23 July 2013 | Proact Stadium | W | 2-1 |
