| 1 | Sat 2 Aug | 21-1 v Accrington StanleyAccrington Stanley 1-1 Gillingham | Sky Bet League Two |
| 2 | Sat 9 Aug | 21-0 v WalsallGillingham 1-0 Walsall | Sky Bet League Two |
| 3 | Tue 12 Aug | 21-1 v AFC WimbledonGillingham 1-1 AFC Wimbledon | Carabao Cup First Round |
| 4 | Sat 16 Aug | 21-1 v Tranmere RoversTranmere Rovers 1-1 Gillingham | Sky Bet League Two |
| 5 | Tue 19 Aug | 24-1 v ChesterfieldGillingham 4-1 Chesterfield | Sky Bet League Two |
| 6 | Sat 23 Aug | 21-0 v Crewe AlexandraGillingham 1-0 Crewe Alexandra | Sky Bet League Two |
| 7 | Sat 30 Aug | 21-0 v Oldham AthleticOldham Athletic 0-1 Gillingham | Sky Bet League Two |
| 8 | Sat 6 Sep | 22-2 v BromleyBromley 2-2 Gillingham | Sky Bet League Two |
| 9 | Sat 13 Sep | 21-0 v Notts CountyGillingham 1-0 Notts County | Sky Bet League Two |
| 10 | Sat 20 Sep | 23-1 v Newport CountyNewport County 1-3 Gillingham | Sky Bet League Two |
| 11 | Sat 27 Sep | 20-1 v Harrogate TownGillingham 0-1 Harrogate Town | Sky Bet League Two |
| 12 | Sat 4 Oct | 2 2-3 v Milton Keynes DonsMilton Keynes Dons 3-2 Gillingham | Sky Bet League Two |
| 13 | Sat 11 Oct | 21-1 v Cheltenham TownGillingham 1-1 Cheltenham Town | Sky Bet League Two |
| 14 | Sat 18 Oct | 2 0-1 v Grimsby TownGrimsby Town 1-0 Gillingham | Sky Bet League Two |
| 15 | Sat 25 Oct | 21-2 v Salford CityGillingham 1-2 Salford City | Sky Bet League Two |
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