| 1 | Sat 9 Aug | 51-0 v WalsallGillingham 1-0 Walsall | Sky Bet League Two |
| 2 | Tue 12 Aug | 51-1 v AFC WimbledonGillingham 1-1 AFC Wimbledon | Carabao Cup First Round |
| 3 | Sat 16 Aug | 51-1 v Tranmere RoversTranmere Rovers 1-1 Gillingham | Sky Bet League Two |
| 4 | Tue 19 Aug | 54-1 v ChesterfieldGillingham 4-1 Chesterfield | Sky Bet League Two |
| 5 | Sat 23 Aug | 51-0 v Crewe AlexandraGillingham 1-0 Crewe Alexandra | Sky Bet League Two |
| 6 | Sat 30 Aug | 51-0 v Oldham AthleticOldham Athletic 0-1 Gillingham | Sky Bet League Two |
| 7 | Sat 6 Sep | 52-2 v BromleyBromley 2-2 Gillingham | Sky Bet League Two |
| 8 | Sat 13 Sep | 5 1-0 v Notts CountyGillingham 1-0 Notts County | Sky Bet League Two |
| 9 | Sat 20 Sep | 5 3-1 v Newport CountyNewport County 1-3 Gillingham | Sky Bet League Two |
| 10 | Sat 27 Sep | 50-1 v Harrogate TownGillingham 0-1 Harrogate Town | Sky Bet League Two |
| 11 | Sat 4 Oct | 5 2-3 v Milton Keynes DonsMilton Keynes Dons 3-2 Gillingham | Sky Bet League Two |
| 12 | Sat 11 Oct | 51-1 v Cheltenham TownGillingham 1-1 Cheltenham Town | Sky Bet League Two |
| 13 | Sat 18 Oct | 50-1 v Grimsby TownGrimsby Town 1-0 Gillingham | Sky Bet League Two |
| 14 | Sat 25 Oct | 51-2 v Salford CityGillingham 1-2 Salford City | Sky Bet League Two |
| 15 | Sat 1 Nov | 52-2 v Newport CountyNewport County 2-2 Gillingham | Emirates FA Cup First Round |
| 16 | Sat 8 Nov | 51-0 v Bristol RoversBristol Rovers 0-1 Gillingham | Sky Bet League Two |
| 17 | Sat 15 Nov | 5 2-2 v Crawley TownGillingham 2-2 Crawley Town | Sky Bet League Two |
| 18 | Sat 13 Dec | 52-2 v BarrowGillingham 2-2 Barrow | Sky Bet League Two |
| 19 | Sat 20 Dec | 51-2 v Fleetwood TownFleetwood Town 2-1 Gillingham | Sky Bet League Two |
| 20 | Fri 26 Dec | 51-1 v Cambridge UnitedGillingham 1-1 Cambridge United | Sky Bet League Two |
| 21 | Mon 29 Dec | 51-1 v Colchester UnitedGillingham 1-1 Colchester United | Sky Bet League Two |
| 22 | Thu 1 Jan | 50-2 v Swindon TownSwindon Town 2-0 Gillingham | Sky Bet League Two |
| 23 | Sat 17 Jan | 5 3-2 v Newport CountyGillingham 3-2 Newport County | Sky Bet League Two |
| 24 | Sat 24 Jan | 53-0 v Harrogate TownHarrogate Town 0-3 Gillingham | Sky Bet League Two |
| 25 | Sat 31 Jan | 51-4 v BromleyGillingham 1-4 Bromley | Sky Bet League Two |
| 26 | Tue 17 Feb | 50-1 v ChesterfieldChesterfield 1-0 Gillingham | Sky Bet League Two |
| 27 | Sat 28 Feb | 51-0 v BarrowBarrow 0-1 Gillingham | Sky Bet League Two |
| 28 | Sat 7 Mar | 51-1 v Fleetwood TownGillingham 1-1 Fleetwood Town | Sky Bet League Two |
| 29 | Tue 10 Mar | 51-5 v Milton Keynes DonsGillingham 1-5 Milton Keynes Dons | Sky Bet League Two |
| 30 | Sat 14 Mar | 5 0-5 v Cambridge UnitedCambridge United 5-0 Gillingham | Sky Bet League Two |
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