| 1 | Sat 2 Aug | 271-1 v Accrington StanleyAccrington Stanley 1-1 Gillingham | Sky Bet League Two |
| 2 | Tue 12 Aug | 271-1 v AFC WimbledonGillingham 1-1 AFC Wimbledon | Carabao Cup First Round |
| 3 | Sat 16 Aug | 271-1 v Tranmere RoversTranmere Rovers 1-1 Gillingham | Sky Bet League Two |
| 4 | Sat 6 Sep | 272-2 v BromleyBromley 2-2 Gillingham | Sky Bet League Two |
| 5 | Sat 8 Nov | 271-0 v Bristol RoversBristol Rovers 0-1 Gillingham | Sky Bet League Two |
| 6 | Tue 11 Nov | 270-3 v Wycombe WanderersGillingham 0-3 Wycombe Wanderers | EFL Trophy Southern Group G |
| 7 | Sat 15 Nov | 272-2 v Crawley TownGillingham 2-2 Crawley Town | Sky Bet League Two |
| 8 | Sat 22 Nov | 27 1-1 v BarnetGillingham 1-1 Barnet | Sky Bet League Two |
| 9 | Sat 29 Nov | 273-3 v Shrewsbury TownShrewsbury Town 3-3 Gillingham | Sky Bet League Two |
| 10 | Sat 13 Dec | 272-2 v BarrowGillingham 2-2 Barrow | Sky Bet League Two |
| 11 | Tue 10 Mar | 271-5 v Milton Keynes DonsGillingham 1-5 Milton Keynes Dons | Sky Bet League Two |
| 12 | Sat 14 Mar | 270-5 v Cambridge UnitedCambridge United 5-0 Gillingham | Sky Bet League Two |
| 13 | Fri 3 Apr | 272-2 v WalsallWalsall 2-2 Gillingham | Sky Bet League Two |
| 14 | Mon 6 Apr | 27 2-0 v Accrington StanleyGillingham 2-0 Accrington Stanley | Sky Bet League Two |
| 15 | Sat 11 Apr | 27 0-0 v Salford CitySalford City 0-0 Gillingham | Sky Bet League Two |
| 16 | Tue 14 Apr | 271-2 v Cheltenham TownCheltenham Town 2-1 Gillingham | Sky Bet League Two |
| 17 | Sat 18 Apr | 271-4 v Grimsby TownGillingham 1-4 Grimsby Town | Sky Bet League Two |
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