| Date | Fixture | Result | Score | Competition |
|---|---|---|---|---|
| 25 Dec 1956 | Liverpool v Leyton Orient | W | 1-0 | League Division Two |
| 26 Dec 1956 | Leyton Orient v Liverpool | W | 0-4 | League Division Two |
| 21 Sep 1957 | Liverpool v Leyton Orient | W | 3-0 | League Division Two |
| 01 Feb 1958 | Leyton Orient v Liverpool | L | 1-0 | League Division Two |
| 08 Nov 1958 | Liverpool v Leyton Orient | W | 3-0 | League Division Two |
| 28 Feb 1959 | Leyton Orient v Liverpool | W | 1-3 | League Division Two |
| 21 Nov 1959 | Liverpool v Leyton Orient | W | 4-3 | League Division Two |
| 09 Jan 1960 | Liverpool v Leyton Orient | W | 2-1 | FA Cup |
| 09 Apr 1960 | Leyton Orient v Liverpool | L | 2-0 | League Division Two |
| 24 Sep 1960 | Leyton Orient v Liverpool | W | 1-3 | League Division Two |
| 11 Feb 1961 | Liverpool v Leyton Orient | W | 5-0 | League Division Two |
| 28 Oct 1961 | Liverpool v Leyton Orient | D | 3-3 | League Division Two |
| 17 Mar 1962 | Leyton Orient v Liverpool | D | 2-2 | League Division Two |
| 17 Nov 1962 | Liverpool v Leyton Orient | W | 5-0 | League Division One |
| 02 May 1963 | Leyton Orient v Liverpool | L | 2-1 | League Division One |