| Date | Fixture | Result | Score | Competition |
|---|---|---|---|---|
| 20 Jan 1940 | Liverpool v Chester | D | 1-1 | West Region War League |
| 18 May 1940 | Chester v Liverpool | L | 4-0 | West Region War League |
| 28 Sep 1940 | Chester v Liverpool | W | 0-2 | North Region War League |
| 05 Oct 1940 | Liverpool v Chester | W | 9-1 | North Region War League |
| 24 May 1941 | Chester v Liverpool | W | 1-6 | North Region War League |
| 08 Nov 1941 | Chester v Liverpool | W | 3-4 | North Region War League |
| 15 Nov 1941 | Liverpool v Chester | W | 4-2 | North Region War League |
| 21 Mar 1942 | Chester v Liverpool | W | 1-3 | North Region War League (Second Championship) |
| 09 May 1942 | Liverpool v Chester | W | 3-0 | North Region War League (Second Championship) |
| 07 Nov 1942 | Liverpool v Chester | W | 4-2 | North Region War League |
| 14 Nov 1942 | Chester v Liverpool | W | 1-5 | North Region War League |
| 03 Apr 1943 | Liverpool v Chester | W | 4-1 | North Region War League (Second Championship) |
| 10 Apr 1943 | Chester v Liverpool | W | 2-5 | North Region War League (Second Championship) |
| 06 Nov 1943 | Chester v Liverpool | L | 3-1 | North Region War League |
| 13 Nov 1943 | Liverpool v Chester | W | 9-0 | North Region War League |
| 19 Feb 1944 | Liverpool v Chester | W | 4-2 | North Region War League (Second Championship) |
| 26 Feb 1944 | Chester v Liverpool | L | 6-0 | North Region War League (Second Championship) |
| 02 Dec 1944 | Liverpool v Chester | W | 6-0 | North Region War League |
| 09 Dec 1944 | Chester v Liverpool | L | 3-2 | North Region War League |
| 05 Jan 1946 | Chester v Liverpool | W | 0-2 | FA Cup |
| 09 Jan 1946 | Liverpool v Chester | W | 2-1 | FA Cup |