Head to Head
| England National League | 2023/04/07 14:00 | Chesterfield v York | L | 1-3 |
| England National League | 2022/10/25 18:45 | York v Chesterfield | D | 1-1 |
Home History
| 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 |
| England National League | 2023/09/30 14:00 | Maidenhead Utd v Chesterfield | D | 1-1 |
| England National League | 2023/09/26 19:00 | Rochdale v Chesterfield | W | 1-2 |
| England National League | 2023/09/23 14:00 | Chesterfield v Wealdstone | W | 3-2 |
| England National League | 2023/09/19 18:45 | Chesterfield v Halifax | W | 3-2 |
| England National League | 2023/09/16 14:00 | Ebbsfleet United v Chesterfield | W | 0-1 |
Away History
| England National League | 2023/10/21 14:00 | Eastleigh v York | L | 3-1 |
| England FA Cup Qualification | 2023/10/17 18:45 | Needham Market v York | W | 0-1 |
| England FA Cup Qualification | 2023/10/14 14:00 | York v Needham Market | D | 0-0 |
| England National League | 2023/10/07 14:00 | York v Bromley | D | 2-2 |
| England National League | 2023/10/03 18:45 | Dag & Red v York | W | 1-2 |
| England National League | 2023/09/30 14:00 | York v Solihull Moors | D | 2-2 |
| England National League | 2023/09/26 18:45 | York v Barnet | L | 2-4 |
| England National League | 2023/09/23 11:30 | Woking v York | W | 1-2 |