Head to Head
| England National League | 2023/04/01 14:00 | Maidenhead Utd v Chesterfield | D | 0-0 |
| England National League | 2022/10/01 14:00 | Chesterfield v Maidenhead Utd | W | 1-2 |
| England National League | 2022/03/19 15:00 | Chesterfield v Maidenhead Utd | L | 1-0 |
| England National League | 2022/01/18 19:45 | Maidenhead Utd v Chesterfield | W | 3-2 |
| England National League | 2021/03/13 15:00 | Maidenhead Utd v Chesterfield | W | 2-0 |
| England National League | 2020/11/14 15:00 | Chesterfield v Maidenhead Utd | W | 1-2 |
| England National League | 2019/08/06 18:45 | Maidenhead Utd v Chesterfield | D | 1-1 |
| England National League | 2019/04/27 11:30 | Maidenhead Utd v Chesterfield | W | 2-0 |
Home History
| England National League | 2023/09/26 18:45 | Maidenhead Utd v Altrincham | L | 0-1 |
| England National League | 2023/09/23 14:00 | Gateshead v Maidenhead Utd | L | 3-0 |
| England National League | 2023/09/19 18:45 | Southend v Maidenhead Utd | L | 2-0 |
| England National League | 2023/09/16 14:00 | Maidenhead Utd v Boreham Wood | L | 0-1 |
| England National League | 2023/09/09 14:00 | Bromley v Maidenhead Utd | L | 4-1 |
| England National League | 2023/09/02 14:00 | Maidenhead Utd v Woking | D | 0-0 |
| England National League | 2023/08/28 14:00 | Kidderminster v Maidenhead Utd | D | 0-0 |
| England National League | 2023/08/26 14:00 | Maidenhead Utd v Oxford City | D | 0-0 |
Away History
| 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 |
| England National League | 2023/09/09 14:00 | Chesterfield v Dag & Red | W | 3-1 |
| England National League | 2023/09/02 14:00 | Aldershot v Chesterfield | W | 3-4 |
| England National League | 2023/08/28 14:00 | Chesterfield v Hartlepool | W | 3-2 |
| England National League | 2023/08/26 14:00 | Altrincham v Chesterfield | L | 2-1 |