Head to Head
| England National League | 2023/08/19 11:30 | Chesterfield v Oldham | D | 1-1 |
| England National League | 2023/02/25 15:00 | Chesterfield v Oldham | W | 0-1 |
| England National League | 2022/09/03 14:00 | Oldham v Chesterfield | L | 0-2 |
| England League 1 | 2017/02/04 15:00 | Chesterfield v Oldham | W | 0-1 |
| England League 1 | 2016/09/10 14:00 | Oldham v Chesterfield | D | 0-0 |
| England League 1 | 2016/03/28 14:00 | Oldham v Chesterfield | W | 1-0 |
| England League 1 | 2015/11/14 15:00 | Chesterfield v Oldham | W | 1-2 |
| England League 1 | 2015/04/18 14:00 | Oldham v Chesterfield | D | 0-0 |
Home History
| England National League | 2024/01/27 15:00 | Oldham v Woking | L | 0-1 |
| England National League | 2024/01/23 19:45 | Oldham v Barnet | W | 2-0 |
| England FA Trophy | 2024/01/13 15:00 | Oldham v Hendon | L | 1-2 |
| England National League | 2024/01/06 15:00 | Dorking Wanderers v Oldham | W | 0-1 |
| England National League | 2023/12/30 15:00 | Oldham v Hartlepool | W | 2-0 |
| England National League | 2023/12/26 15:00 | Hartlepool v Oldham | W | 1-3 |
| England National League | 2023/12/23 15:00 | Oldham v Gateshead | L | 1-2 |
| England National League | 2023/12/16 15:00 | Solihull Moors v Oldham | W | 2-3 |
Away History
| England National League | 2024/01/27 15:00 | Chesterfield v Southend | W | 3-0 |
| England National League | 2024/01/23 19:45 | Chesterfield v Woking | W | 1-0 |
| England National League | 2024/01/16 19:45 | Chesterfield v Altrincham | W | 2-1 |
| England FA Trophy | 2024/01/13 15:00 | Welling v Chesterfield | L | 2-0 |
| England National League | 2024/01/10 19:45 | Chesterfield v Gateshead | W | 5-0 |
| England FA Cup | 2024/01/06 15:00 | Watford v Chesterfield | L | 2-1 |
| England National League | 2024/01/01 15:00 | Chesterfield v Solihull Moors | W | 3-2 |
| England National League | 2023/12/26 15:00 | Solihull Moors v Chesterfield | L | 2-0 |
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