| 1 | Sat 6 Sep | 172-2 v BromleyBromley 2-2 Gillingham | Sky Bet League Two |
| 2 | Sat 13 Sep | 171-0 v Notts CountyGillingham 1-0 Notts County | Sky Bet League Two |
| 3 | Sat 20 Sep | 173-1 v Newport CountyNewport County 1-3 Gillingham | Sky Bet League Two |
| 4 | Sat 27 Sep | 170-1 v Harrogate TownGillingham 0-1 Harrogate Town | Sky Bet League Two |
| 5 | Tue 11 Nov | 170-3 v Wycombe WanderersGillingham 0-3 Wycombe Wanderers | EFL Trophy Southern Group G |
| 6 | Sat 15 Nov | 172-2 v Crawley TownGillingham 2-2 Crawley Town | Sky Bet League Two |
| 7 | Thu 1 Jan | 170-2 v Swindon TownSwindon Town 2-0 Gillingham | Sky Bet League Two |
| 8 | Sat 17 Jan | 173-2 v Newport CountyGillingham 3-2 Newport County | Sky Bet League Two |
| 9 | Sat 24 Jan | 173-0 v Harrogate TownHarrogate Town 0-3 Gillingham | Sky Bet League Two |
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