| 1 | Sat 20 Sep | 123-1 v Newport CountyNewport County 1-3 Gillingham | Sky Bet League Two |
| 2 | Sat 27 Sep | 120-1 v Harrogate TownGillingham 0-1 Harrogate Town | Sky Bet League Two |
| 3 | Sat 4 Oct | 122-3 v Milton Keynes DonsMilton Keynes Dons 3-2 Gillingham | Sky Bet League Two |
| 4 | Sat 11 Oct | 121-1 v Cheltenham TownGillingham 1-1 Cheltenham Town | Sky Bet League Two |
| 5 | Sat 18 Oct | 120-1 v Grimsby TownGrimsby Town 1-0 Gillingham | Sky Bet League Two |
| 6 | Sat 25 Oct | 121-2 v Salford CityGillingham 1-2 Salford City | Sky Bet League Two |
| 7 | Sat 1 Nov | 122-2 v Newport CountyNewport County 2-2 Gillingham | Emirates FA Cup First Round |
| 8 | Sat 8 Nov | 121-0 v Bristol RoversBristol Rovers 0-1 Gillingham | Sky Bet League Two |
| 9 | Tue 11 Nov | 120-3 v Wycombe WanderersGillingham 0-3 Wycombe Wanderers | EFL Trophy Southern Group G |
| 10 | Sat 22 Nov | 121-1 v BarnetGillingham 1-1 Barnet | Sky Bet League Two |
| 11 | Sat 29 Nov | 123-3 v Shrewsbury TownShrewsbury Town 3-3 Gillingham | Sky Bet League Two |
| 12 | Sat 6 Dec | 120-0 v Colchester UnitedColchester United 0-0 Gillingham | Sky Bet League Two |
| 13 | Sat 13 Dec | 122-2 v BarrowGillingham 2-2 Barrow | Sky Bet League Two |
| 14 | Sat 20 Dec | 121-2 v Fleetwood TownFleetwood Town 2-1 Gillingham | Sky Bet League Two |
| 15 | Fri 26 Dec | 121-1 v Cambridge UnitedGillingham 1-1 Cambridge United | Sky Bet League Two |
| 16 | Mon 29 Dec | 121-1 v Colchester UnitedGillingham 1-1 Colchester United | Sky Bet League Two |
| 17 | Thu 1 Jan | 120-2 v Swindon TownSwindon Town 2-0 Gillingham | Sky Bet League Two |
| 18 | Sat 24 Jan | 123-0 v Harrogate TownHarrogate Town 0-3 Gillingham | Sky Bet League Two |
| 19 | Tue 3 Feb | 120-1 v Notts CountyNotts County 1-0 Gillingham | Sky Bet League Two |
| 20 | Sat 7 Feb | 122-1 v Tranmere RoversGillingham 2-1 Tranmere Rovers | Sky Bet League Two |
| 21 | Sat 14 Feb | 120-1 v Crewe AlexandraCrewe Alexandra 1-0 Gillingham | Sky Bet League Two |
| 22 | Tue 17 Feb | 120-1 v ChesterfieldChesterfield 1-0 Gillingham | Sky Bet League Two |
| 23 | Sat 21 Feb | 120-3 v Oldham AthleticGillingham 0-3 Oldham Athletic | Sky Bet League Two |
| 24 | Sat 28 Feb | 121-0 v BarrowBarrow 0-1 Gillingham | Sky Bet League Two |
| 25 | Sat 7 Mar | 121-1 v Fleetwood TownGillingham 1-1 Fleetwood Town | Sky Bet League Two |
| 26 | Tue 10 Mar | 121-5 v Milton Keynes DonsGillingham 1-5 Milton Keynes Dons | Sky Bet League Two |
| 27 | Sat 14 Mar | 120-5 v Cambridge UnitedCambridge United 5-0 Gillingham | Sky Bet League Two |
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