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 FA Cup Qualification | 2023/10/14 14:00 | Altrincham v Oldham | W | 0-1 |
| England National League | 2023/10/07 14:00 | Oldham v Dag & Red | D | 1-1 |
| England National League | 2023/10/03 18:45 | Oldham v Maidenhead Utd | D | 1-1 |
| England National League | 2023/09/30 14:00 | Wealdstone v Oldham | D | 1-1 |
| England National League | 2023/09/26 18:45 | Kidderminster v Oldham | W | 1-2 |
| England National League | 2023/09/23 14:00 | Oldham v Oxford City | W | 4-0 |
| England National League | 2023/09/19 18:45 | Oldham v York | W | 2-0 |
| England National League | 2023/09/16 14:00 | Bromley v Oldham | L | 3-0 |
Away History
| England FA Cup Qualification | 2023/10/14 14:00 | Chesterfield v Kettering | W | 5-0 |
| England National League | 2023/10/07 14:00 | Boreham Wood v Chesterfield | W | 0-2 |
| England National League | 2023/10/03 18:45 | Chesterfield v Bromley | W | 2-0 |
| England National League | 2023/09/30 14:00 | Maidenhead Utd v Chesterfield | D | 1-1 |
| England National League | 2023/09/26 19:00 | Rochdale v Chesterfield | W | 1-2 |
| England National League | 2023/09/23 14:00 | Chesterfield v Wealdstone | W | 3-2 |
| England National League | 2023/09/19 18:45 | Chesterfield v Halifax | W | 3-2 |
| England National League | 2023/09/16 14:00 | Ebbsfleet United v Chesterfield | W | 0-1 |
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