Head to Head
| England National League | 2023/11/21 19:45 | Woking v Chesterfield | W | 0-2 |
| England National League | 2023/03/18 12:30 | Woking v Chesterfield | W | 0-1 |
| England National League | 2023/02/07 19:45 | Chesterfield v Woking | L | 1-3 |
| England National League | 2022/05/15 14:00 | Chesterfield v Woking | D | 0-0 |
| England National League | 2021/09/28 18:45 | Woking v Chesterfield | L | 3-1 |
| England National League | 2021/05/08 14:00 | Woking v Chesterfield | W | 1-4 |
| England National League | 2020/10/10 14:00 | Chesterfield v Woking | W | 4-0 |
| England National League | 2019/08/13 18:45 | Chesterfield v Woking | L | 1-2 |
Home History
| 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 |
| England FA Cup | 2024/01/06 15:00 | Watford v Chesterfield | L | 2-1 |
| England National League | 2024/01/01 15:00 | Chesterfield v Solihull Moors | W | 3-2 |
| England National League | 2023/12/26 15:00 | Solihull Moors v Chesterfield | L | 2-0 |
| England National League | 2023/12/23 15:00 | Chesterfield v Aldershot | W | 4-1 |
| England National League | 2023/12/16 15:00 | Hartlepool v Chesterfield | W | 0-1 |
Away History
| England National League | 2024/01/06 15:00 | Solihull Moors v Woking | L | 3-0 |
| England National League | 2024/01/01 15:00 | Woking v Aldershot | L | 2-3 |
| England National League | 2023/12/26 15:00 | Aldershot v Woking | D | 0-0 |
| England National League | 2023/12/23 15:00 | Woking v Maidenhead Utd | D | 0-0 |
| England National League | 2023/12/16 15:00 | Dorking Wanderers v Woking | W | 1-2 |
| England FA Trophy | 2023/12/12 19:45 | Weston Super Mare v Woking | L | 3-2 |
| England National League | 2023/11/25 15:00 | Boreham Wood v Woking | L | 4-2 |
| England National League | 2023/11/21 19:45 | Woking v Chesterfield | L | 0-2 |