| L1 | 2024-2025 | 10/08/2024 | Leyton Orient | 1-2 | Bolton Wanderers | Dion Charles, Victor Adeboyejo | Highlights | 7,835 | Win |
| L1 | 2023-2024 | 20/01/2024 | Leyton Orient | 1-0 | Bolton Wanderers | | Highlights | 8,642 | Loss |
| L1 | 2023-2024 | 23/12/2023 | Bolton Wanderers | 3-2 | Leyton Orient | Josh Dacres-Cogley, Dion Charles, George Thomason | Highlights | 21,482 | Win |
| L2 | 2020-2021 | 30/01/2021 | Bolton Wanderers | 2-0 | Leyton Orient | Own Goal, Eoin Doyle | Highlights | Unknown | Win |
| L2 | 2020-2021 | 31/10/2020 | Leyton Orient | 4-0 | Bolton Wanderers | | Highlights | Unknown | Loss |
| LC2L2 | 1997-1998 | 30/09/1997 | Bolton Wanderers | 4-4 | Leyton Orient | Blake 2, McGinlay (pen), Gunnlaugsson | | 6,444 | Draw |
| LC2L1 | 1997-1998 | 16/09/1997 | Leyton Orient | 1-3 | Bolton Wanderers | Todd, Frandsen, McGinlay | | 4,128 | Win |
| D2 | 1992-1993 | 06/03/1993 | Bolton Wanderers | 1-0 | Leyton Orient | Walker A | | 7,763 | Win |
| D2 | 1992-1993 | 03/10/1992 | Leyton Orient | 1-0 | Bolton Wanderers | | | 3,946 | Loss |
| D3 | 1991-1992 | 26/12/1991 | Leyton Orient | 2-1 | Bolton Wanderers | Green | | 4,896 | Loss |
| D3 | 1991-1992 | 31/08/1991 | Bolton Wanderers | 1-0 | Leyton Orient | Reeves | | 5,058 | Win |
| D3 | 1990-1991 | 20/04/1991 | Bolton Wanderers | 1-0 | Leyton Orient | Reeves | | 7,926 | Win |
| D3 | 1990-1991 | 20/10/1990 | Leyton Orient | 0-1 | Bolton Wanderers | Storer | | 4,121 | Win |
| D3 | 1989-1990 | 27/03/1990 | Leyton Orient | 0-0 | Bolton Wanderers | | | 3,296 | Draw |
| D3 | 1989-1990 | 23/09/1989 | Bolton Wanderers | 2-1 | Leyton Orient | Cowdrill, Philliskirk | | 5,951 | Win |
| D4 | 1987-1988 | 02/04/1988 | Leyton Orient | 1-2 | Bolton Wanderers | Darby, May | | 4,537 | Win |
| D4 | 1987-1988 | 07/11/1987 | Bolton Wanderers | 1-0 | Leyton Orient | Thomas J | | 5,189 | Win |
| D2 | 1965-1966 | 26/03/1966 | Bolton Wanderers | 2-0 | Leyton Orient | Rimmer W, Lee F (pen) | | 8,713 | Win |
| D2 | 1965-1966 | 02/10/1965 | Leyton Orient | 1-0 | Bolton Wanderers | | | 7,774 | Loss |
| D2 | 1964-1965 | 24/04/1965 | Bolton Wanderers | 0-0 | Leyton Orient | | | 9,016 | Draw |
| D2 | 1964-1965 | 28/09/1964 | Leyton Orient | 3-1 | Bolton Wanderers | Lee F | | 11,385 | Loss |
| D1 | 1962-1963 | 15/04/1963 | Bolton Wanderers | 0-1 | Leyton Orient | | | 16,752 | Loss |
| D1 | 1962-1963 | 12/04/1963 | Leyton Orient | 0-1 | Bolton Wanderers | Butler D (pen) | | 15,389 | Win |