| 1 | Tue 19 Aug | 32 4-1 v ChesterfieldGillingham 4-1 Chesterfield | Sky Bet League Two |
| 2 | Sat 23 Aug | 32 1-0 v Crewe AlexandraGillingham 1-0 Crewe Alexandra | Sky Bet League Two |
| 3 | Sat 4 Oct | 322-3 v Milton Keynes DonsMilton Keynes Dons 3-2 Gillingham | Sky Bet League Two |
| 4 | Sat 11 Oct | 321-1 v Cheltenham TownGillingham 1-1 Cheltenham Town | Sky Bet League Two |
| 5 | Sat 18 Oct | 320-1 v Grimsby TownGrimsby Town 1-0 Gillingham | Sky Bet League Two |
| 6 | Sat 1 Nov | 32 2-2 v Newport CountyNewport County 2-2 Gillingham | Emirates FA Cup First Round |
| 7 | Sat 29 Nov | 32 3-3 v Shrewsbury TownShrewsbury Town 3-3 Gillingham | Sky Bet League Two |
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