| L1 | 2021-2022 | 05/03/2022 | Gillingham | 0-3 | Bolton Wanderers | Aaron Morley, Declan John, Jon Dadi Bodvarsson | Highlights | 5,109 | Win |
| L1 | 2021-2022 | 23/10/2021 | Bolton Wanderers | 2-2 | Gillingham | Oladapo Afolayan, Keiran Lee | Highlights | 13,807 | Draw |
| L1 | 2019-2020 | 31/08/2019 | Gillingham | 5-0 | Bolton Wanderers | | Highlights | 5,065 | Loss |
| L1 | 2016-2017 | 14/03/2017 | Gillingham | 0-4 | Bolton Wanderers | David Wheater, Adam Le Fondre, Mark Beevers, Josh Vela | Highlights | 5,199 | Win |
| L1 | 2016-2017 | 12/12/2016 | Bolton Wanderers | 4-0 | Gillingham | Gary Madine (2), Josh Vela, Sammy Ameobi | Highlights | 13,861 | Win |
| LC3 | 2003-2004 | 28/10/2003 | Bolton Wanderers | 2-0 | Gillingham | Giannakopoulos, Pedersen | | 5,258 | Win |
| D1 | 2000-2001 | 10/03/2001 | Bolton Wanderers | 3-3 | Gillingham | Frandsen, Patterson (og), Holdsworth | | 13,161 | Draw |
| D1 | 2000-2001 | 06/10/2000 | Gillingham | 2-2 | Bolton Wanderers | Hansen, O'Kane | | 9,311 | Draw |
| LC2L2 | 1999-2000 | 21/09/1999 | Bolton Wanderers | 2-0 | Gillingham | Hansen, Holdsworth | | 3,673 | Win |
| LC2L1 | 1999-2000 | 14/09/1999 | Gillingham | 1-4 | Bolton Wanderers | Cox, Gudjohnsen 2, Bergsson | | 4,996 | Win |
| D3 | 1988-1989 | 04/04/1989 | Gillingham | 0-1 | Bolton Wanderers | Thomas J | | 3,096 | Win |
| D3 | 1988-1989 | 06/01/1989 | Bolton Wanderers | 2-1 | Gillingham | Stevens I, Thompson S (pen) | | 4,178 | Win |
| D3 | 1986-1987 | 09/05/1987 | Gillingham | 1-0 | Bolton Wanderers | | | 5,561 | Loss |
| D3 | 1986-1987 | 13/12/1986 | Bolton Wanderers | 3-0 | Gillingham | Caldwell 2, Gavin | | 4,867 | Win |
| D3 | 1985-1986 | 11/01/1986 | Bolton Wanderers | 0-1 | Gillingham | | | 5,232 | Loss |
| D3 | 1985-1986 | 31/08/1985 | Gillingham | 2-1 | Bolton Wanderers | Cross | | 2,773 | Loss |
| D3 | 1984-1985 | 20/04/1985 | Gillingham | 2-3 | Bolton Wanderers | Caldwell, Chandler, Oghani | | 5,132 | Win |
| D3 | 1984-1985 | 24/11/1984 | Bolton Wanderers | 1-2 | Gillingham | Chandler | | 4,381 | Loss |
| D3 | 1983-1984 | 07/04/1984 | Bolton Wanderers | 0-1 | Gillingham | | | 4,815 | Loss |
| D3 | 1983-1984 | 06/09/1983 | Gillingham | 2-0 | Bolton Wanderers | | | 3,087 | Loss |