| L1 | 2023-2024 | 23/01/2024 | Bolton Wanderers | 1-0 | Cheltenham Town | Victor Adeboyejo | Highlights | 19,309 | Win |
| L1 | 2023-2024 | 12/08/2023 | Cheltenham Town | 0-3 | Bolton Wanderers | Dion Charles, Own Goal, Dion Charles | Highlights | 4,898 | Win |
| L1 | 2022-2023 | 04/02/2023 | Bolton Wanderers | 1-0 | Cheltenham Town | Kyle Dempsey | Highlights | 17,736 | Win |
| L1 | 2022-2023 | 04/10/2022 | Cheltenham Town | 1-0 | Bolton Wanderers | | Highlights | 3,988 | Loss |
| L1 | 2021-2022 | 23/04/2022 | Cheltenham Town | 1-2 | Bolton Wanderers | Keiran Sadlier, Amadou Bakayoko | Highlights | 5,228 | Win |
| L1 | 2021-2022 | 27/11/2021 | Bolton Wanderers | 2-2 | Cheltenham Town | Xavier Amaechi, Elias Kachunga | Highlights | 13,145 | Draw |
| L2 | 2020-2021 | 16/01/2021 | Bolton Wanderers | 1-1 | Cheltenham Town | Eoin Doyle | Highlights | Unknown | Draw |
| L2 | 2020-2021 | 15/12/2020 | Cheltenham Town | 0-1 | Bolton Wanderers | Ryan Delaney | Highlights | Unknown | Win |
| EFLT | 2016-2017 | 08/11/2016 | Cheltenham Town | 1-0 | Bolton Wanderers | | Highlights | 1,038 | Loss |