Head to Head
| England National League | 2023/03/18 12:30 | Woking v Chesterfield | L | 0-1 |
| England National League | 2023/02/07 19:45 | Chesterfield v Woking | W | 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 | W | 3-1 |
| England National League | 2021/05/08 14:00 | Woking v Chesterfield | L | 1-4 |
| England National League | 2020/10/10 14:00 | Chesterfield v Woking | L | 4-0 |
| England National League | 2019/08/13 18:45 | Chesterfield v Woking | W | 1-2 |
Home History
| England National League | 2023/11/18 15:00 | Woking v Oldham | L | 0-1 |
| England National League | 2023/11/11 15:00 | Oxford City v Woking | L | 3-2 |
| England FA Cup | 2023/11/04 15:00 | Ramsgate v Woking | L | 2-1 |
| England National League | 2023/10/28 14:00 | Woking v Bromley | L | 0-1 |
| England National League | 2023/10/24 18:45 | Eastleigh v Woking | W | 0-1 |
| England National League | 2023/10/21 14:00 | Dag & Red v Woking | L | 2-1 |
| England FA Cup Qualification | 2023/10/17 18:45 | Woking v Hemel Hempstead | W | 2-0 |
| England FA Cup Qualification | 2023/10/14 14:00 | Hemel Hempstead v Woking | D | 0-0 |
Away History
| England National League | 2023/11/18 15:00 | Southend v Chesterfield | L | 2-1 |
| England National League | 2023/11/11 15:00 | Chesterfield v Barnet | W | 4-2 |
| England FA Cup | 2023/11/05 12:15 | Chesterfield v Portsmouth | W | 1-0 |
| England National League | 2023/10/28 14:00 | Kidderminster v Chesterfield | W | 1-3 |
| England National League | 2023/10/24 18:45 | Chesterfield v York | W | 4-0 |
| 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 |