Home History
| Club Friendly List | 2018/07/07 11:00 | Gainsborough v Barnsley | L | 0-2 |
| England National League North | 2018/04/28 14:00 | Gainsborough v Tamworth | W | 3-0 |
| England National League North | 2018/04/21 14:00 | AFC Telford v Gainsborough | L | 3-2 |
| England National League North | 2018/04/17 18:45 | North Ferriby v Gainsborough | W | 0-1 |
| England National League North | 2018/04/14 14:00 | Gainsborough v York | W | 1-0 |
| England National League North | 2018/04/11 18:45 | Curzon Ashton v Gainsborough | L | 2-0 |
| England National League North | 2018/04/07 14:00 | Salford City v Gainsborough | L | 1-0 |
| England National League North | 2018/03/30 14:00 | Gainsborough v Spennymoor Town | W | 4-1 |
Away History
| Club Friendly List | 2018/07/14 14:00 | Boston Utd v Chesterfield | D | 1-1 |
| Club Friendly List | 2018/07/07 11:00 | Sheffield FC v Chesterfield | W | 1-5 |
| England League 2 | 2018/05/05 14:00 | Barnet v Chesterfield | L | 3-0 |
| England League 2 | 2018/05/01 18:45 | Chesterfield v Newport County | W | 1-0 |
| England League 2 | 2018/04/28 14:00 | Chesterfield v Wycombe | L | 1-2 |
| England League 2 | 2018/04/21 14:00 | Forest Green v Chesterfield | L | 4-1 |
| England League 2 | 2018/04/17 18:45 | Exeter v Chesterfield | L | 2-1 |
| England League 2 | 2018/04/14 12:00 | Chesterfield v Mansfield | L | 0-1 |