Head to Head
| England League 2 | 2025/04/18 14:00 | Cheltenham v Gillingham | D | 1-1 |
| England League 2 | 2024/12/20 19:45 | Gillingham v Cheltenham | D | 2-2 |
| England League 1 | 2022/04/15 14:00 | Cheltenham v Gillingham | D | 2-2 |
| England League 1 | 2021/11/23 19:45 | Gillingham v Cheltenham | W | 0-2 |
| England FA Cup | 2021/11/16 19:45 | Cheltenham v Gillingham | W | 1-0 |
| England FA Cup | 2021/11/06 14:00 | Gillingham v Cheltenham | D | 1-1 |
| England EFL Cup | 2021/08/24 18:45 | Gillingham v Cheltenham | W | 5-6 |
Home History
| England League 2 | 2025/09/06 14:00 | Cheltenham v Accrington Stanley | W | 1-0 |
| England EFL Trophy | 2025/09/02 18:00 | Plymouth v Cheltenham | L | 2-0 |
| England League 2 | 2025/08/29 18:45 | Salford City v Cheltenham | D | 1-1 |
| England EFL Cup | 2025/08/26 18:45 | Cardiff v Cheltenham | L | 3-0 |
| England League 2 | 2025/08/23 14:00 | Cheltenham v Barnet | L | 0-1 |
| England League 2 | 2025/08/19 18:45 | Cheltenham v Bromley | L | 1-2 |
| England League 2 | 2025/08/16 14:00 | Milton Keynes Dons v Cheltenham | L | 5-0 |
| England EFL Cup | 2025/08/13 18:45 | Cheltenham v Exeter | W | 2-0 |
Away History
| England League 2 | 2025/09/06 16:30 | Bromley v Gillingham | D | 2-2 |
| England EFL Trophy | 2025/09/02 18:00 | Gillingham v Fulham U21 | W | 4-1 |
| England League 2 | 2025/08/30 14:00 | Oldham v Gillingham | W | 0-1 |
| England League 2 | 2025/08/23 14:00 | Gillingham v Crewe | W | 1-0 |
| England League 2 | 2025/08/19 18:45 | Gillingham v Chesterfield | W | 4-1 |
| England League 2 | 2025/08/16 14:00 | Tranmere v Gillingham | D | 1-1 |
| England EFL Cup | 2025/08/12 18:45 | Gillingham v AFC Wimbledon | L | 3-5 |
| England League 2 | 2025/08/09 14:00 | Gillingham v Walsall | W | 1-0 |
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