Home History
| England League 1 | 2014/09/20 14:00 | Gillingham v Walsall | D | 0-0 |
| England League 1 | 2014/09/16 18:45 | Gillingham v Peterborough | W | 2-1 |
| England League 1 | 2014/09/13 14:00 | Oldham v Gillingham | D | 0-0 |
| England League 1 | 2014/09/05 18:45 | Coventry v Gillingham | L | 1-0 |
| England EFL Trophy | 2014/09/02 18:45 | Stevenage v Gillingham | W | 0-1 |
| England League 1 | 2014/08/30 14:00 | Gillingham v Crewe | W | 2-0 |
| England EFL Cup | 2014/08/26 18:45 | Gillingham v Newcastle | L | 0-1 |
| England League 1 | 2014/08/23 14:00 | Barnsley v Gillingham | L | 4-1 |
Away History
| England League 1 | 2014/09/20 14:00 | Doncaster v Chesterfield | L | 3-2 |
| England League 1 | 2014/09/16 18:45 | Preston v Chesterfield | D | 3-3 |
| England League 1 | 2014/09/13 14:00 | Chesterfield v Scunthorpe | W | 4-1 |
| England EFL Trophy | 2014/09/02 18:45 | Scunthorpe v Chesterfield | L | 2-0 |
| England League 1 | 2014/08/30 14:00 | Port Vale v Chesterfield | W | 1-2 |
| England League 1 | 2014/08/23 14:00 | Fleetwood Town v Chesterfield | D | 0-0 |
| England League 1 | 2014/08/19 18:45 | Chesterfield v Milton Keynes Dons | L | 0-1 |
| England League 1 | 2014/08/16 14:00 | Chesterfield v Rochdale | W | 2-1 |