| L1 | 2023-2024 | 27/01/2024 | Carlisle United | 1-4 | Bolton Wanderers | Zac Ashworth, Paris Maghoma, Kyle Dempsey, Nathanael Ogbeta | Highlights | 11,443 | Win |
| L1 | 2023-2024 | 07/10/2023 | Bolton Wanderers | 1-3 | Carlisle United | Own Goal | Highlights | 23,187 | Loss |
| L2 | 2020-2021 | 20/04/2021 | Bolton Wanderers | 1-0 | Carlisle United | Eoin Doyle | Highlights | Unknown | Win |
| L2 | 2020-2021 | 26/12/2020 | Carlisle United | 3-3 | Bolton Wanderers | George Thomason, Nathan Delfouneso, Peter Kioso | Highlights | Unknown | Draw |
| D4 | 1987-1988 | 05/03/1988 | Carlisle United | 0-2 | Bolton Wanderers | Thomas J (pen), Brookman | | 2,796 | Win |
| D4 | 1987-1988 | 17/10/1987 | Bolton Wanderers | 5-0 | Carlisle United | Brookman 2, Darby, Elliott S, Wright (og) | | 4,184 | Win |
| D3 | 1986-1987 | 18/04/1987 | Bolton Wanderers | 2-0 | Carlisle United | Neal, Stevens I | | 4,241 | Win |
| D3 | 1986-1987 | 03/02/1987 | Carlisle United | 0-0 | Bolton Wanderers | | | 2,535 | Draw |
| D2 | 1982-1983 | 05/04/1983 | Carlisle United | 5-0 | Bolton Wanderers | | | 5,615 | Loss |
| D2 | 1982-1983 | 27/12/1982 | Bolton Wanderers | 1-0 | Carlisle United | Jones P | | 8,171 | Win |
| LC1L2 | 1982-1983 | 14/09/1982 | Bolton Wanderers | 4-0 | Carlisle United | Henry 2 (1 pen), Doyle, Moores I | | 4,039 | Win |
| LC1L1 | 1982-1983 | 31/08/1982 | Carlisle United | 3-3 | Bolton Wanderers | Doyle, Hoggan, Moores I | | 4,314 | Draw |
| D2 | 1976-1977 | 22/03/1977 | Bolton Wanderers | 3-4 | Carlisle United | Allardyce, Whatmore 2 | | 18,471 | Loss |
| D2 | 1976-1977 | 06/11/1976 | Carlisle United | 0-1 | Bolton Wanderers | Jones P | | 8,811 | Win |
| D2 | 1975-1976 | 21/02/1976 | Carlisle United | 3-2 | Bolton Wanderers | Reid, Allardyce | | 12,809 | Loss |
| D2 | 1975-1976 | 15/11/1975 | Bolton Wanderers | 0-0 | Carlisle United | | | 14,556 | Draw |
| D2 | 1973-1974 | 23/02/1974 | Bolton Wanderers | 2-0 | Carlisle United | Byrom, Jones G (pen) | | 16,675 | Win |
| D2 | 1973-1974 | 06/10/1973 | Carlisle United | 1-0 | Bolton Wanderers | | | 8,365 | Loss |
| D2 | 1970-1971 | 10/04/1971 | Bolton Wanderers | 0-3 | Carlisle United | | | 8,038 | Loss |
| D2 | 1970-1971 | 26/12/1970 | Carlisle United | 1-0 | Bolton Wanderers | | | 11,132 | Loss |
| D2 | 1969-1970 | 04/04/1970 | Bolton Wanderers | 0-0 | Carlisle United | | | 9,120 | Draw |
| D2 | 1969-1970 | 26/08/1969 | Carlisle United | 2-1 | Bolton Wanderers | Wharton | | 11,682 | Loss |
| D2 | 1968-1969 | 26/12/1968 | Bolton Wanderers | 0-1 | Carlisle United | | | 13,922 | Loss |
| D2 | 1968-1969 | 05/10/1968 | Carlisle United | 1-1 | Bolton Wanderers | Hill | | 8,846 | Draw |
| D2 | 1967-1968 | 20/01/1968 | Carlisle United | 3-0 | Bolton Wanderers | | | 11,065 | Loss |
| D2 | 1967-1968 | 16/09/1967 | Bolton Wanderers | 2-3 | Carlisle United | Greaves, Bromley | | 12,809 | Loss |
| D2 | 1966-1967 | 13/05/1967 | Carlisle United | 6-1 | Bolton Wanderers | Lee F | | 8,493 | Loss |
| D2 | 1966-1967 | 07/09/1966 | Bolton Wanderers | 3-0 | Carlisle United | Davies W 3 | | 15,282 | Win |
| D2 | 1965-1966 | 04/05/1966 | Bolton Wanderers | 4-0 | Carlisle United | Hatton D 2, Lee F, Taylor G | | 6,536 | Win |
| D2 | 1965-1966 | 30/10/1965 | Carlisle United | 1-1 | Bolton Wanderers | Hill | | 11,114 | Draw |
| FAC3 | 1930-1931 | 10/01/1931 | Bolton Wanderers | 1-0 | Carlisle United | Blackmore | | 23,029 | Win |