| Date | Fixture | Result | Score | Competition |
|---|---|---|---|---|
| 10 Sep 1904 | Chesterfield Town v Liverpool | D | 1-1 | League Division Two |
| 07 Jan 1905 | Liverpool v Chesterfield Town | W | 6-1 | League Division Two |
| 23 Jan 1932 | Chesterfield v Liverpool | W | 2-4 | FA Cup |
| 21 Apr 1945 | Liverpool v Chesterfield | D | 0-0 | North Region War League (Second Championship) |
| 28 Apr 1945 | Chesterfield v Liverpool | L | 1-0 | North Region War League (Second Championship) |
| 15 Dec 1945 | Chesterfield v Liverpool | D | 1-1 | North Region War League |
| 22 Dec 1945 | Liverpool v Chesterfield | D | 2-2 | North Region War League |
| 25 Sep 1979 | Liverpool v Chesterfield | W | 3-1 | League Cup |
| 22 Sep 1992 | Liverpool v Chesterfield | D | 4-4 | League Cup |
| 06 Oct 1992 | Chesterfield v Liverpool | W | 1-4 | League Cup |