Head to Head
| England League 2 | 2024/08/31 11:30 | Gillingham v Chesterfield | L | 1-0 |
| England League 1 | 2017/02/14 19:45 | Gillingham v Chesterfield | D | 1-1 |
| England League 1 | 2016/09/27 18:45 | Chesterfield v Gillingham | D | 3-3 |
| England League 1 | 2016/02/27 15:00 | Gillingham v Chesterfield | W | 1-2 |
| England League 1 | 2015/10/10 14:00 | Chesterfield v Gillingham | L | 1-3 |
| England League 1 | 2015/03/17 19:45 | Chesterfield v Gillingham | W | 3-0 |
| England League 1 | 2014/12/20 15:00 | Gillingham v Chesterfield | W | 2-3 |
Home History
| England League 2 | 2025/02/06 19:45 | Chesterfield v Doncaster | W | 5-2 |
| England League 2 | 2025/02/01 12:30 | Cheltenham v Chesterfield | L | 1-0 |
| England League 2 | 2025/01/28 19:45 | Chesterfield v Bromley | W | 3-0 |
| England League 2 | 2025/01/25 15:00 | Chesterfield v Port Vale | D | 1-1 |
| England League 2 | 2025/01/18 15:00 | Grimsby v Chesterfield | D | 1-1 |
| England EFL Trophy | 2025/01/14 19:00 | Chesterfield v Rotherham | D | 0-0 |
| England League 2 | 2025/01/01 15:00 | Chesterfield v Milton Keynes Dons | L | 1-2 |
| England League 2 | 2024/12/29 15:00 | Bradford v Chesterfield | L | 2-1 |
Away History
| England League 2 | 2025/02/08 15:00 | Barrow v Gillingham | L | 3-0 |
| England League 2 | 2025/02/01 12:30 | Gillingham v Notts County | L | 1-2 |
| England League 2 | 2025/01/28 19:45 | Grimsby v Gillingham | D | 1-1 |
| England League 2 | 2025/01/25 15:00 | Tranmere v Gillingham | D | 1-1 |
| England League 2 | 2025/01/18 12:30 | Gillingham v Doncaster | L | 0-1 |
| England League 2 | 2025/01/02 19:45 | Gillingham v Bromley | L | 0-3 |
| England League 2 | 2024/12/30 20:00 | AFC Wimbledon v Gillingham | L | 1-0 |
| England League 2 | 2024/12/26 15:00 | Colchester v Gillingham | L | 2-0 |