Head to Head
| England National League | 2023/02/25 15:00 | Chesterfield v Oldham | L | 0-1 |
| England National League | 2022/09/03 14:00 | Oldham v Chesterfield | W | 0-2 |
| England League 1 | 2017/02/04 15:00 | Chesterfield v Oldham | L | 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 | L | 1-0 |
| England League 1 | 2015/11/14 15:00 | Chesterfield v Oldham | L | 1-2 |
| England League 1 | 2015/04/18 14:00 | Oldham v Chesterfield | D | 0-0 |
| England League 1 | 2014/10/18 14:00 | Chesterfield v Oldham | D | 1-1 |
Home History
| England National League | 2023/08/15 18:45 | Oxford City v Chesterfield | W | 1-2 |
| England National League | 2023/08/12 14:00 | AFC Fylde v Chesterfield | W | 2-4 |
| England National League | 2023/08/05 14:00 | Chesterfield v Dorking Wanderers | W | 4-3 |
| Europe Friendlies | 2023/07/29 12:00 | Bristol Rovers v Chesterfield | L | 2-0 |
| Club Friendly List | 2023/07/22 14:00 | Accrington Stanley v Chesterfield | W | 2-3 |
| Club Friendly List | 2023/07/19 18:00 | Chesterfield v Derby | L | 0-1 |
| Club Friendly List | 2023/07/15 14:00 | Chesterfield v Sheff Utd | L | 0-2 |
| Club Friendly List | 2023/07/11 18:00 | Chesterfield v Sheff Wed | L | 1-2 |
Away History
| England National League | 2023/08/15 18:45 | Oldham v Halifax | L | 1-2 |
| England National League | 2023/08/12 14:00 | Oldham v Aldershot | W | 5-1 |
| England National League | 2023/08/05 14:00 | Southend v Oldham | L | 4-0 |
| Club Friendly List | 2023/07/29 14:00 | Oldham v Mansfield | L | 0-3 |
| Club Friendly List | 2023/07/25 18:45 | Barrow v Oldham | D | 1-1 |
| Club Friendly List | 2023/07/22 14:00 | Curzon Ashton v Oldham | W | 1-2 |
| Club Friendly List | 2023/07/18 18:45 | Chorley v Oldham | W | 1-6 |
| Club Friendly List | 2023/07/15 14:00 | Southport v Oldham | D | 1-1 |