| First Team Matches | Second Team Matches | Associated with both clubs | Transfers |
As Chester
| Seasons | Competition | Date | Venue | Results | Wolves Manager | Chester Manager | Referee | |
| 1941/42 | War Competition | 27 December 1941 | Molineux | W | 2-1 | Major Frank Buckley | A Sewell (Coventry) | |
| 1941/42 | War Competition | 3 January 1942 | Sealand Road | W | 3-1 | Major Frank Buckley | P Snape (Manchester) | |
| 1941/42 | War Competition | 4 April 1942 | Molineux | W | 3-1 | Major Frank Buckley | A Baker (Crewe) | |
| 1941/42 | War Competition | 6 April 1942 | Sealand Road | W | 1-0 | Major Frank Buckley | Unknown | |
| 1943/44 | War Competition | 15 April 1944 | Sealand Road | W | 3-1 | Ted Vizard | E Evans (Liverpool) | |
| 1943/44 | War Competition | 22 April 1944 | Molineux | L | 0-4 | Ted Vizard | A Baker (Crewe) | |
| 1944/45 | War Competition | 20 January 1945 | Molineux | W | 6-1 | Ted Vizard | C Barrick (Brayfield, Northants) | |
| 1944/45 | War Competition | 17 March 1945 | Sealand Road | W | 4-0 | Ted Vizard | S Boardman (Hale) |
As Chester City
| 1976/77 | FA Cup | 26 February 1977 | Molineux | W | 1-0 | Sammy Chung | Alan Oakes | P Partridge (Bishop Auckland) |
| 1985/86 | Friendly | 7 August 1985 | Away | L | 2-3 | Sammy Chapman © | Caretaker* | x |
| 1988/89 | Football League (3) | 2 January 1989 | Molineux | W | 3-1 | Graham Turner | Harry McNally | K Breen (Maghull, Liverpool) |
| 1988/89 | Football League (3) | 25 March 1989 | Sealand Road | D | 1-1 | Graham Turner | Harry McNally | K Lupton (Stockton on Tees) |
| 2005/06 | FL Cup | 23 August 2005 | Molineux | W | 5-1 | Glen Hoddle | Keith Curle | A Leake (Darwen) |
