Head to Head
| England League 2 | 2024/12/21 15:00 | Chesterfield v AFC Wimbledon | L | 1-0 |
| England FA Cup | 2022/11/26 15:00 | AFC Wimbledon v Chesterfield | L | 0-2 |
| England League 1 | 2017/01/21 15:00 | Chesterfield v AFC Wimbledon | D | 0-0 |
| England League 1 | 2016/09/03 14:00 | AFC Wimbledon v Chesterfield | W | 2-1 |
Home History
| England League 2 | 2024/12/21 15:00 | Chesterfield v AFC Wimbledon | L | 1-0 |
| England League 2 | 2024/12/14 15:00 | AFC Wimbledon v Doncaster | W | 1-0 |
| England EFL Trophy | 2024/12/10 19:45 | Colchester v AFC Wimbledon | L | 2-0 |
| England League 2 | 2024/12/07 15:00 | Harrogate Town v AFC Wimbledon | W | 0-3 |
| England League 2 | 2024/12/03 19:45 | AFC Wimbledon v Newport County | D | 2-2 |
| England FA Cup | 2024/11/30 19:15 | AFC Wimbledon v Dag & Red | L | 1-2 |
| England League 2 | 2024/11/26 19:45 | Tranmere v AFC Wimbledon | W | 0-2 |
| England League 2 | 2024/11/23 15:00 | AFC Wimbledon v Walsall | L | 0-1 |
Away History
| England League 2 | 2024/12/21 15:00 | Chesterfield v AFC Wimbledon | W | 1-0 |
| England League 2 | 2024/12/14 15:00 | Carlisle v Chesterfield | W | 0-2 |
| England EFL Trophy | 2024/12/10 19:00 | Chesterfield v Wigan | W | 3-2 |
| England League 2 | 2024/12/07 15:00 | Chesterfield v Tranmere | W | 3-0 |
| England League 2 | 2024/12/03 19:45 | Milton Keynes Dons v Chesterfield | L | 3-0 |
| England FA Cup | 2024/11/30 15:00 | Exeter v Chesterfield | L | 2-0 |
| England League 2 | 2024/11/23 15:00 | Chesterfield v Barrow | W | 1-0 |
| England League 2 | 2024/11/16 15:00 | Harrogate Town v Chesterfield | L | 2-1 |