| 1 | Sat 29 Aug | 11-1 v Northampton TownGillingham 1-1 Northampton Town | Sky Bet League Two |
| 2 | Sat 5 Sep | 14-1 v RochdaleRochdale 1-4 Gillingham | Sky Bet League Two |
| 3 | Sat 12 Sep | 12-0 v Tranmere RoversGillingham 2-0 Tranmere Rovers | Sky Bet League Two |
| 4 | Sat 19 Sep | 13-0 v Bristol RoversGillingham 3-0 Bristol Rovers | Sky Bet League Two |
| 5 | Sat 26 Sep | 10-3 v York CityYork City 3-0 Gillingham | Sky Bet League Two |
| 6 | Sat 3 Oct | 10-0 v Newport CountyGillingham 0-0 Newport County | Sky Bet League Two |
| 7 | Sat 10 Oct | 14-1 v Rotherham UnitedRotherham United 1-4 Gillingham | Sky Bet League Two |
| 8 | Sat 17 Oct | 11-3 v Accrington StanleyAccrington Stanley 3-1 Gillingham | Sky Bet League Two |
| 9 | Tue 20 Oct | 11-1 v Port ValeGillingham 1-1 Port Vale | Sky Bet League Two |
| 10 | Sat 24 Oct | 11-4 v Grimsby TownGillingham 1-4 Grimsby Town | Sky Bet League Two |
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