| 1 | Tue 3 Sep | 61-2 v Peterborough UnitedGillingham 1-2 Peterborough United | EFL Trophy Southern Group D |
| 2 | Sat 7 Sep | 60-1 v Doncaster RoversDoncaster Rovers 1-0 Gillingham | Sky Bet League Two |
| 3 | Sat 14 Sep | 6 3-0 v Tranmere RoversGillingham 3-0 Tranmere Rovers | Sky Bet League Two |
| 4 | Sat 28 Sep | 62-0 v BarrowGillingham 2-0 Barrow | Sky Bet League Two |
| 5 | Tue 1 Oct | 60-1 v Grimsby TownGillingham 0-1 Grimsby Town | Sky Bet League Two |
| 6 | Sat 5 Oct | 60-2 v Crewe AlexandraCrewe Alexandra 2-0 Gillingham | Sky Bet League Two |
| 7 | Sat 12 Oct | 61-2 v Accrington StanleyGillingham 1-2 Accrington Stanley | Sky Bet League Two |
| 8 | Sat 19 Oct | 6 1-2 v Bradford CityBradford City 2-1 Gillingham | Sky Bet League Two |
| 9 | Tue 22 Oct | 6 0-2 v Newport CountyGillingham 0-2 Newport County | Sky Bet League Two |
| 10 | Tue 12 Nov | 61-1 v StevenageStevenage 1-1 Gillingham | EFL Trophy Southern Group D |
| 11 | Sat 23 Nov | 61-2 v Harrogate TownGillingham 1-2 Harrogate Town | Sky Bet League Two |
| 12 | Wed 4 Dec | 61-2 v BromleyBromley 2-1 Gillingham | Sky Bet League Two |
| 13 | Sat 7 Dec | 61-0 v Salford CityGillingham 1-0 Salford City | Sky Bet League Two |
| 14 | Sat 14 Dec | 61-0 v Milton Keynes DonsMilton Keynes Dons 0-1 Gillingham | Sky Bet League Two |
| 15 | Fri 20 Dec | 62-2 v Cheltenham TownGillingham 2-2 Cheltenham Town | Sky Bet League Two |
| 16 | Thu 26 Dec | 60-2 v Colchester UnitedColchester United 2-0 Gillingham | Sky Bet League Two |
| 17 | Mon 30 Dec | 60-1 v AFC WimbledonAFC Wimbledon 1-0 Gillingham | Sky Bet League Two |
| 18 | Thu 2 Jan | 60-3 v BromleyGillingham 0-3 Bromley | Sky Bet League Two |
| 19 | Sat 18 Jan | 60-1 v Doncaster RoversGillingham 0-1 Doncaster Rovers | Sky Bet League Two |
| 20 | Sat 26 Apr | 61-1 v Swindon TownGillingham 1-1 Swindon Town | Sky Bet League Two |
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