| First Team Matches | Second Team Matches | Associated with both clubs | Transfers |
| Season | Competition | Date | Venue | Result | ||
| 1941/42 | War Time | 27 December 1941 | Molineux | W | 2-1 | Known as Chester |
| 1941/42 | War Time | 3 January 1942 | Sealand Road | W | 3-1 | |
 |
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| 1941/42 | War Time | 4 April 1942 | Molineux | W | 3-1 | |
| 1941/42 | War Time | 6 April 1942 | Sealand Road | W | 1-0 | |
| 1943/44 | War Time | 15 April 1944 | Sealand Road | W | 3-1 | |
| 1943/44 | War Time | 22 April 1944 | Molineux | L | 0-4 | |
 |
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| 1944/45 | War Time | 20 January 1945 | Molineux | W | 6-1 | |
| 1944/45 | War Time | 17 March 1945 | Sealand Road | W | 4-0 | |
| 1976/77 | FAC5 | 26 February 1977 | Molineux | W | 1-0 | Known as Chester City |
| 1985/86 | Friendly | 7 August 1985 | Sealand Road | L | 2-3 | |
 |
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| 1988/89 | Division 3 | 2 January 1989 | Molineux | W | 3-1 | |
| 1988/89 | Division 3 | 25 March 1989 | Sealand Road | D | 1-1 | |
| 2005/06 | FLC1 | 23 August 2005 | Molineux | W | 5-1 |
