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
| England National League | 2021/09/11 14:00 | Wrexham v Woking | L | 1-0 |
| England National League | 2021/08/30 14:00 | Torquay v Woking | W | 0-4 |
| England National League | 2021/08/28 14:00 | Woking v Halifax | L | 2-3 |
| England National League | 2021/08/21 14:00 | Wealdstone v Woking | W | 1-2 |
| Club Friendly List | 2021/08/07 14:00 | Hampton & Richmond v Woking | D | 1-1 |
| Club Friendly List | 2021/08/03 18:45 | Farnborough v Woking | L | 2-1 |
| Club Friendly List | 2021/07/27 18:30 | Woking v AFC Wimbledon | W | 1-0 |
| UK Friendlies | 2021/07/16 18:45 | Woking v West Brom | L | 0-1 |
Away History
| England National League | 2021/09/14 18:45 | Chesterfield v Barnet | W | 4-2 |
| England National League | 2021/09/11 14:00 | Dover v Chesterfield | D | 0-0 |
| England National League | 2021/09/04 14:00 | Chesterfield v Bromley | D | 2-2 |
| England National League | 2021/08/30 14:00 | Kings Lynn Town v Chesterfield | W | 0-2 |
| England National League | 2021/08/28 14:00 | Chesterfield v Wealdstone | W | 2-0 |
| England National League | 2021/08/21 14:00 | Aldershot v Chesterfield | W | 0-2 |
| UK Friendlies | 2021/08/14 13:00 | Chesterfield v Grimsby | W | 2-1 |
| Club Friendly List | 2021/07/31 14:00 | Chesterfield v Port Vale | L | 0-1 |