Head to Head
| England National League | 2024/03/16 12:30 | Oldham v Chesterfield | D | 2-2 |
| 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 |
Home History
| England League 2 | 2025/10/04 14:00 | Notts County v Oldham | L | 3-1 |
| England League 2 | 2025/09/27 11:30 | Oldham v Barnet | D | 1-1 |
| England League 2 | 2025/09/20 14:00 | Cheltenham v Oldham | W | 0-3 |
| England League 2 | 2025/09/13 14:00 | Oldham v Bromley | W | 1-0 |
| England League 2 | 2025/09/06 14:00 | Cambridge Utd v Oldham | W | 0-1 |
| England League 2 | 2025/08/30 14:00 | Oldham v Gillingham | L | 0-1 |
| England EFL Trophy | 2025/08/26 18:00 | Oldham v Man City U21 | L | 1-5 |
| England League 2 | 2025/08/23 14:00 | Fleetwood Town v Oldham | D | 1-1 |
Away History
| England League 2 | 2025/10/04 14:00 | Colchester v Chesterfield | L | 6-2 |
| England League 2 | 2025/09/27 14:00 | Chesterfield v Newport County | W | 4-1 |
| England League 2 | 2025/09/20 14:00 | Bromley v Chesterfield | D | 2-2 |
| England League 2 | 2025/09/13 14:00 | Chesterfield v Milton Keynes Dons | D | 1-1 |
| England League 2 | 2025/09/06 14:00 | Walsall v Chesterfield | L | 1-0 |
| England EFL Trophy | 2025/09/02 18:00 | Crewe v Chesterfield | L | 7-1 |
| England League 2 | 2025/08/30 14:00 | Chesterfield v Crawley Town | D | 2-2 |
| England League 2 | 2025/08/23 14:00 | Harrogate Town v Chesterfield | W | 1-2 |
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