| 1 | Sat 8 Aug | 30-3 v Luton TownGillingham 0-3 Luton Town | Carabao Cup First Round |
| 2 | Sat 22 Aug | 30-0 v Fleetwood TownFleetwood Town 0-0 Gillingham | Sky Bet League Two |
| 3 | Sat 29 Aug | 31-1 v Northampton TownGillingham 1-1 Northampton Town | Sky Bet League Two |
| 4 | Tue 1 Sep | 31-1 v ChesterfieldChesterfield 1-1 Gillingham | Sky Bet League Two |
| 5 | Sat 5 Sep | 3 4-1 v RochdaleRochdale 1-4 Gillingham | Sky Bet League Two |
| 6 | Sat 12 Sep | 3 2-0 v Tranmere RoversGillingham 2-0 Tranmere Rovers | Sky Bet League Two |
| 7 | Tue 20 Oct | 3 1-1 v Port ValeGillingham 1-1 Port Vale | Sky Bet League Two |
| 8 | Sat 24 Oct | 31-4 v Grimsby TownGillingham 1-4 Grimsby Town | Sky Bet League Two |
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