| 1 | Sat 10 Aug | 54-1 v Carlisle UnitedGillingham 4-1 Carlisle United | Sky Bet League Two |
| 2 | Tue 13 Aug | 51-3 v Swansea CitySwansea City 3-1 Gillingham | Carabao Cup First Round |
| 3 | Sat 17 Aug | 51-0 v MorecambeMorecambe 0-1 Gillingham | Sky Bet League Two |
| 4 | Sat 24 Aug | 5 0-0 v Fleetwood TownFleetwood Town 0-0 Gillingham | Sky Bet League Two |
| 5 | Sat 31 Aug | 5 1-0 v ChesterfieldGillingham 1-0 Chesterfield | Sky Bet League Two |
| 6 | Tue 3 Sep | 5 1-2 v Peterborough UnitedGillingham 1-2 Peterborough United | EFL Trophy Southern Group D |
| 7 | Sat 14 Sep | 53-0 v Tranmere RoversGillingham 3-0 Tranmere Rovers | Sky Bet League Two |
| 8 | Sat 21 Sep | 5 1-0 v Notts CountyNotts County 0-1 Gillingham | Sky Bet League Two |
| 9 | Sat 28 Sep | 52-0 v BarrowGillingham 2-0 Barrow | Sky Bet League Two |
| 10 | Tue 1 Oct | 50-1 v Grimsby TownGillingham 0-1 Grimsby Town | Sky Bet League Two |
| 11 | Sat 5 Oct | 50-2 v Crewe AlexandraCrewe Alexandra 2-0 Gillingham | Sky Bet League Two |
| 12 | Sat 12 Oct | 51-2 v Accrington StanleyGillingham 1-2 Accrington Stanley | Sky Bet League Two |
| 13 | Sat 19 Oct | 51-2 v Bradford CityBradford City 2-1 Gillingham | Sky Bet League Two |
| 14 | Tue 22 Oct | 50-2 v Newport CountyGillingham 0-2 Newport County | Sky Bet League Two |
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