Head to Head
| England League 2 | 2025/08/09 14:00 | Cheltenham v Chesterfield | W | 0-2 |
| England League 2 | 2025/02/01 12:30 | Cheltenham v Chesterfield | L | 1-0 |
| England League 2 | 2024/09/21 11:30 | Chesterfield v Cheltenham | D | 1-1 |
| England League 2 | 2018/03/17 15:00 | Cheltenham v Chesterfield | D | 1-1 |
| England League 2 | 2017/09/30 14:00 | Chesterfield v Cheltenham | L | 0-2 |
Home History
| England FA Cup | 2025/12/06 19:30 | Chesterfield v Doncaster | L | 1-2 |
| England EFL Trophy | 2025/12/02 19:00 | Doncaster v Chesterfield | L | 5-1 |
| England League 2 | 2025/11/29 15:00 | Chesterfield v Swindon | L | 1-2 |
| England League 2 | 2025/11/22 15:00 | Crewe v Chesterfield | D | 3-3 |
| England League 2 | 2025/11/15 15:00 | Grimsby v Chesterfield | W | 0-1 |
| England EFL Trophy | 2025/11/11 19:00 | Chesterfield v Liverpool U21 | D | 2-2 |
| England League 2 | 2025/11/08 15:00 | Chesterfield v Accrington Stanley | D | 3-3 |
| England FA Cup | 2025/11/01 15:00 | Stevenage v Chesterfield | W | 0-1 |
Away History
| England FA Cup | 2025/12/06 15:00 | Cheltenham v Buxton | W | 6-2 |
| England League 2 | 2025/11/29 15:00 | Colchester v Cheltenham | L | 2-0 |
| England League 2 | 2025/11/22 15:00 | Cheltenham v Bristol Rovers | W | 1-0 |
| England League 2 | 2025/11/15 15:00 | Tranmere v Cheltenham | L | 3-2 |
| England League 2 | 2025/11/10 20:00 | Cheltenham v Notts County | L | 1-2 |
| England FA Cup | 2025/11/01 15:00 | Cheltenham v Bradford | W | 1-0 |
| England EFL Trophy | 2025/10/28 19:00 | Cheltenham v Tottenham U21 | D | 2-2 |
| England League 2 | 2025/10/25 11:30 | Cheltenham v Walsall | W | 1-0 |
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