| 1 | Sat 8 Aug | 140-3 v Luton TownGillingham 0-3 Luton Town | Carabao Cup First Round |
| 2 | Sat 15 Aug | 14 0-3 v WalsallGillingham 0-3 Walsall | Sky Bet League Two |
| 3 | Sat 22 Aug | 140-0 v Fleetwood TownFleetwood Town 0-0 Gillingham | Sky Bet League Two |
| 4 | Sat 29 Aug | 14 1-1 v Northampton TownGillingham 1-1 Northampton Town | Sky Bet League Two |
| 5 | Tue 1 Sep | 141-1 v ChesterfieldChesterfield 1-1 Gillingham | Sky Bet League Two |
| 6 | Sat 5 Sep | 144-1 v RochdaleRochdale 1-4 Gillingham | Sky Bet League Two |
| 7 | Sat 12 Sep | 14 2-0 v Tranmere RoversGillingham 2-0 Tranmere Rovers | Sky Bet League Two |
| 8 | Sat 19 Sep | 143-0 v Bristol RoversGillingham 3-0 Bristol Rovers | Sky Bet League Two |
| 9 | Sat 26 Sep | 14 0-3 v York CityYork City 3-0 Gillingham | Sky Bet League Two |
| 10 | Sat 3 Oct | 140-0 v Newport CountyGillingham 0-0 Newport County | Sky Bet League Two |
| 11 | Sat 10 Oct | 144-1 v Rotherham UnitedRotherham United 1-4 Gillingham | Sky Bet League Two |
| 12 | Sat 17 Oct | 141-3 v Accrington StanleyAccrington Stanley 3-1 Gillingham | Sky Bet League Two |
| 13 | Sat 24 Oct | 141-4 v Grimsby TownGillingham 1-4 Grimsby Town | Sky Bet League Two |
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