Head to Head
| England FA Cup | 2018/12/02 14:00 | Chesterfield v Grimsby | L | 0-2 |
| England League 2 | 2018/04/07 14:00 | Grimsby v Chesterfield | L | 1-0 |
| England League 2 | 2017/08/05 14:00 | Chesterfield v Grimsby | L | 1-3 |
Home History
| Club Friendly List | 2021/07/31 14:00 | Chesterfield v Port Vale | L | 0-1 |
| Club Friendly List | 2021/07/27 18:30 | Chesterfield v Bradford | W | 2-1 |
| 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 |
Away History
| World Club Friendlies | 2021/08/07 14:00 | Boston Utd v Grimsby | W | 0-1 |
| Club Friendly List | 2021/08/03 18:45 | Alfreton Town v Grimsby | W | 0-1 |
| Club Friendly List | 2021/07/30 18:00 | Hyde Utd v Grimsby | L | 2-0 |
| Club Friendly List | 2021/07/24 12:00 | Grimsby v Rotherham | L | 0-1 |
| UK Friendlies | 2021/07/17 13:00 | Cleethorpes Town v Grimsby | W | 1-4 |
| England League 2 | 2021/05/08 14:00 | Cambridge Utd v Grimsby | L | 3-0 |
| England League 2 | 2021/05/01 14:00 | Grimsby v Port Vale | W | 1-0 |
| England League 2 | 2021/04/27 18:00 | Exeter v Grimsby | L | 3-2 |