Head to Head
| 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
| UK Friendlies | 2021/07/16 18:45 | Woking v West Brom | L | 0-1 |
| England National League | 2021/05/29 11:30 | Woking v Wealdstone | L | 2-4 |
| England National League | 2021/05/22 14:00 | Stockport v Woking | D | 1-1 |
| England National League | 2021/05/15 14:00 | Solihull Moors v Woking | L | 2-1 |
| England National League | 2021/05/11 19:00 | Sutton Utd v Woking | L | 3-2 |
| England National League | 2021/05/08 14:00 | Woking v Chesterfield | L | 1-4 |
| England National League | 2021/05/03 14:00 | Dag & Red v Woking | L | 3-1 |
| England National League | 2021/05/01 14:00 | Woking v Weymouth | L | 2-4 |
Away History
| Club Friendly List | 2021/07/21 18:30 | Matlock Town v Chesterfield | W | 1-3 |
| UK Friendlies | 2021/07/17 14:00 | Alfreton Town v Chesterfield | L | 3-2 |
| England National League | 2021/06/05 15:00 | Notts County v Chesterfield | L | 3-2 |
| England National League | 2021/05/29 11:30 | Halifax v Chesterfield | W | 1-2 |
| England National League | 2021/05/22 14:00 | Chesterfield v Dag & Red | W | 2-1 |
| England National League | 2021/05/15 14:00 | Chesterfield v Wealdstone | D | 0-0 |
| England National League | 2021/05/11 18:45 | Chesterfield v Kings Lynn Town | W | 4-1 |
| England National League | 2021/05/08 14:00 | Woking v Chesterfield | W | 1-4 |