Head to Head
| 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 |
| England National League | 2018/09/25 18:45 | Chesterfield v Maidenhead Utd | W | 1-3 |
Home History
| England National League | 2022/01/08 15:00 | Aldershot v Maidenhead Utd | D | 1-1 |
| England National League | 2021/12/28 15:00 | Maidenhead Utd v Bromley | W | 1-0 |
| England National League | 2021/12/11 15:00 | Maidenhead Utd v Solihull Moors | L | 0-4 |
| England National League | 2021/12/07 19:45 | Southend v Maidenhead Utd | D | 1-1 |
| England National League | 2021/12/04 15:00 | Barnet v Maidenhead Utd | L | 3-0 |
| England National League | 2021/11/20 15:00 | Boreham Wood v Maidenhead Utd | L | 4-0 |
| England National League | 2021/11/13 15:00 | Maidenhead Utd v Dag & Red | L | 1-4 |
| England FA Cup | 2021/11/06 15:00 | Halifax v Maidenhead Utd | L | 7-4 |
Away History
| England National League | 2022/01/15 15:00 | Barnet v Chesterfield | W | 1-4 |
| England FA Cup | 2022/01/08 17:30 | Chelsea v Chesterfield | L | 5-1 |
| England National League | 2022/01/01 15:00 | Chesterfield v Kings Lynn Town | W | 1-0 |
| England National League | 2021/12/28 15:00 | Chesterfield v Halifax | D | 1-1 |
| England National League | 2021/12/11 15:00 | Grimsby v Chesterfield | W | 0-1 |
| England FA Cup | 2021/12/05 17:15 | Salford City v Chesterfield | W | 0-2 |
| England National League | 2021/11/23 19:45 | Chesterfield v Altrincham | D | 2-2 |
| England National League | 2021/11/20 15:00 | Solihull Moors v Chesterfield | W | 0-2 |