Head to Head
| England National League | 2023/09/30 14:00 | Maidenhead Utd v Chesterfield | D | 1-1 |
| 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 | L | 1-2 |
| England National League | 2022/03/19 15:00 | Chesterfield v Maidenhead Utd | W | 1-0 |
| England National League | 2022/01/18 19:45 | Maidenhead Utd v Chesterfield | L | 3-2 |
| England National League | 2021/03/13 15:00 | Maidenhead Utd v Chesterfield | L | 2-0 |
| England National League | 2020/11/14 15:00 | Chesterfield v Maidenhead Utd | L | 1-2 |
| England National League | 2019/08/06 18:45 | Maidenhead Utd v Chesterfield | D | 1-1 |
Home History
| England National League | 2024/02/10 15:00 | Chesterfield v Ebbsfleet United | D | 2-2 |
| England National League | 2024/02/06 19:45 | Dag & Red v Chesterfield | W | 1-2 |
| England National League | 2024/02/03 15:00 | Eastleigh v Chesterfield | W | 1-3 |
| England National League | 2024/01/27 15:00 | Chesterfield v Southend | W | 3-0 |
| England National League | 2024/01/23 19:45 | Chesterfield v Woking | W | 1-0 |
| England National League | 2024/01/16 19:45 | Chesterfield v Altrincham | W | 2-1 |
| England FA Trophy | 2024/01/13 15:00 | Welling v Chesterfield | L | 2-0 |
| England National League | 2024/01/10 19:45 | Chesterfield v Gateshead | W | 5-0 |
Away History
| England National League | 2024/02/13 19:45 | Halifax v Maidenhead Utd | L | 2-1 |
| England National League | 2024/02/10 15:00 | Boreham Wood v Maidenhead Utd | L | 1-0 |
| England National League | 2024/02/06 19:45 | Wealdstone v Maidenhead Utd | W | 0-1 |
| England National League | 2024/02/03 15:00 | York v Maidenhead Utd | D | 1-1 |
| England National League | 2024/01/27 15:00 | Maidenhead Utd v Solihull Moors | W | 2-1 |
| England National League | 2024/01/23 19:45 | Maidenhead Utd v Ebbsfleet United | L | 0-1 |
| England National League | 2024/01/06 15:00 | Maidenhead Utd v Bromley | D | 0-0 |
| England National League | 2023/12/26 15:00 | Maidenhead Utd v Wealdstone | L | 0-2 |
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