Home History
| England National League | 2019/08/10 14:00 | Boreham Wood v Chesterfield | D | 2-2 |
| England National League | 2019/08/06 18:45 | Maidenhead Utd v Chesterfield | D | 1-1 |
| England National League | 2019/08/03 14:00 | Chesterfield v Dover | L | 1-2 |
| Club Friendly List | 2019/07/27 14:00 | Chesterfield v Burton Albion | L | 2-5 |
| Club Friendly List | 2019/07/24 18:30 | Sheffield FC v Chesterfield | L | 2-1 |
| Elite Club Friendlies | 2019/07/23 18:30 | Chesterfield v Sheff Utd | L | 0-5 |
| Club Friendly List | 2019/07/20 14:00 | Chesterfield v Rotherham | L | 1-2 |
| Club Friendly List | 2019/07/16 18:30 | Matlock Town v Chesterfield | W | 1-2 |
Away History
| England National League | 2019/08/10 14:00 | Woking v Harrogate Town | W | 1-0 |
| England National League | 2019/08/06 18:45 | Woking v Aldershot | L | 0-1 |
| England National League | 2019/08/03 14:00 | Dag & Red v Woking | W | 0-2 |
| Club Friendly List | 2019/07/30 18:45 | Woking v Portsmouth | L | 2-4 |
| Club Friendly List | 2019/07/27 14:00 | Farnborough v Woking | W | 1-3 |
| Club Friendly List | 2019/07/20 14:00 | Dunston UTS v Woking | D | 1-1 |
| Club Friendly List | 2019/07/19 19:15 | Salford City v Woking | W | 1-3 |
| Club Friendly List | 2019/07/16 18:45 | Woking v Wycombe | L | 2-3 |