| EFLF | 2022-2023 | 02/04/2023 | Plymouth Argyle | 0-4 | Bolton Wanderers | Kyle Dempsey, Dion Charles, Elias Kachunga, Gethin Jones | Highlights | 79,389 | Win |
| L1 | 2022-2023 | 07/01/2023 | Bolton Wanderers | 0-0 | Plymouth Argyle | | Highlights | 18,638 | Draw |
| L1 | 2022-2023 | 27/08/2022 | Plymouth Argyle | 2-0 | Bolton Wanderers | | Highlights | 14,631 | Loss |
| L1 | 2021-2022 | 12/03/2022 | Bolton Wanderers | 0-1 | Plymouth Argyle | | Highlights | 16,078 | Loss |
| L1 | 2021-2022 | 19/10/2021 | Plymouth Argyle | 3-0 | Bolton Wanderers | | Highlights | 12,813 | Loss |
| FAC1 | 2019-2020 | 09/11/2019 | Bolton Wanderers | 0-1 | Plymouth Argyle | | Highlights | 6,992 | Loss |
| D2 | 1992-1993 | 16/01/1993 | Bolton Wanderers | 3-1 | Plymouth Argyle | Walker A, Seagraves, Morrison (og) | | 8,256 | Win |
| D2 | 1992-1993 | 26/09/1992 | Plymouth Argyle | 2-1 | Bolton Wanderers | Darby | | 6,829 | Loss |
| D3 | 1985-1986 | 22/04/1986 | Plymouth Argyle | 4-1 | Bolton Wanderers | Sutton | | 12,183 | Loss |
| D3 | 1985-1986 | 28/09/1985 | Bolton Wanderers | 3-1 | Plymouth Argyle | Joyce W G, Caldwell, Rudge | | 4,270 | Win |
| D3 | 1984-1985 | 09/02/1985 | Plymouth Argyle | 2-0 | Bolton Wanderers | | | 4,978 | Loss |
| D3 | 1984-1985 | 22/09/1984 | Bolton Wanderers | 7-2 | Plymouth Argyle | Caldwell 3, Oghani, Joyce W G, Chandler 2 (1 pen) | | 3,876 | Win |
| D3 | 1983-1984 | 16/04/1984 | Bolton Wanderers | 2-1 | Plymouth Argyle | Chandler (pen), Bell G | | 3,266 | Win |
| D3 | 1983-1984 | 12/11/1983 | Plymouth Argyle | 2-0 | Bolton Wanderers | | | 4,624 | Loss |
| D2 | 1976-1977 | 05/03/1977 | Bolton Wanderers | 3-0 | Plymouth Argyle | Whatmore 2, Jones P (pen) | | 18,496 | Win |
| D2 | 1976-1977 | 25/09/1976 | Plymouth Argyle | 1-1 | Bolton Wanderers | Mariner (og) | | 12,564 | Draw |
| D2 | 1975-1976 | 13/03/1976 | Bolton Wanderers | 0-0 | Plymouth Argyle | | | 21,147 | Draw |
| D2 | 1975-1976 | 11/10/1975 | Plymouth Argyle | 2-3 | Bolton Wanderers | Whatmore 2, Reid | | 14,595 | Win |
| D3 | 1972-1973 | 27/01/1973 | Plymouth Argyle | 1-0 | Bolton Wanderers | | | 8,592 | Loss |
| D3 | 1972-1973 | 09/09/1972 | Bolton Wanderers | 2-0 | Plymouth Argyle | Byrom, Jones G (pen) | | 5,515 | Win |
| D3 | 1971-1972 | 29/01/1972 | Bolton Wanderers | 2-1 | Plymouth Argyle | Greaves, Seddon I | | 5,856 | Win |
| D3 | 1971-1972 | 12/10/1971 | Plymouth Argyle | 2-0 | Bolton Wanderers | | | 13,336 | Loss |
| D2 | 1967-1968 | 04/05/1968 | Plymouth Argyle | 1-2 | Bolton Wanderers | Hill, Wharton (pen) | | 5,371 | Win |
| D2 | 1967-1968 | 09/12/1967 | Bolton Wanderers | 1-2 | Plymouth Argyle | Taylor G | | 9,505 | Loss |
| D2 | 1966-1967 | 22/04/1967 | Bolton Wanderers | 1-2 | Plymouth Argyle | Phillips R | | 7,427 | Loss |
| D2 | 1966-1967 | 26/11/1966 | Plymouth Argyle | 2-0 | Bolton Wanderers | | | 13,635 | Loss |
| D2 | 1965-1966 | 05/02/1966 | Bolton Wanderers | 0-1 | Plymouth Argyle | | | 10,705 | Loss |
| D2 | 1965-1966 | 28/08/1965 | Plymouth Argyle | 1-3 | Bolton Wanderers | Davies W 2, Taylor G | | 16,444 | Win |
| D2 | 1964-1965 | 06/02/1965 | Plymouth Argyle | 1-3 | Bolton Wanderers | Lee F, Bromley, Taylor G | | 14,553 | Win |
| D2 | 1964-1965 | 26/09/1964 | Bolton Wanderers | 6-1 | Plymouth Argyle | Hill 2, Davies W 2, Bromley, Taylor G | | 13,670 | Win |
| D2 | 1934-1935 | 06/04/1935 | Plymouth Argyle | 1-0 | Bolton Wanderers | | | 16,238 | Loss |
| FAC4 | 1934-1935 | 26/01/1935 | Plymouth Argyle | 1-4 | Bolton Wanderers | Milsom 2, Westwood, McNeil (og) | | 41,403 | Win |
| D2 | 1934-1935 | 24/11/1934 | Bolton Wanderers | 3-2 | Plymouth Argyle | Milsom, Westwood 2 | | 18,210 | Win |
| D2 | 1933-1934 | 06/01/1934 | Plymouth Argyle | 3-0 | Bolton Wanderers | | | 18,348 | Loss |
| D2 | 1933-1934 | 02/09/1933 | Bolton Wanderers | 2-0 | Plymouth Argyle | Westwood, Hughes J | | 11,388 | Win |