| 1 | Sat 5 Aug | 31-0 v Stockport CountyStockport County 0-1 Gillingham | Sky Bet League Two |
| 2 | Tue 29 Aug | 32-3 v Luton TownLuton Town 3-2 Gillingham | Carabao Cup Second Round |
| 3 | Tue 5 Sep | 32-1 v Leyton OrientGillingham 2-1 Leyton Orient | EFL Trophy |
| 4 | Sat 7 Oct | 32-1 v Milton Keynes DonsGillingham 2-1 Milton Keynes Dons | Sky Bet League Two |
| 5 | Tue 10 Oct | 31-5 v PortsmouthPortsmouth 5-1 Gillingham | EFL Trophy |
| 6 | Sat 14 Oct | 3 1-4 v WalsallWalsall 4-1 Gillingham | Sky Bet League Two |
| 7 | Sat 21 Oct | 31-2 v Notts CountyGillingham 1-2 Notts County | Sky Bet League Two |
| 8 | Sat 4 Nov | 32-0 v HerefordHereford 0-2 Gillingham | Emirates FA Cup First Round |
| 9 | Sat 18 Nov | 3 3-1 v Salford CityGillingham 3-1 Salford City | Sky Bet League Two |
| 10 | Fri 29 Dec | 31-0 v Sutton UnitedGillingham 1-0 Sutton United | Sky Bet League Two |
| 11 | Sat 13 Jan | 32-1 v Accrington StanleyAccrington Stanley 1-2 Gillingham | Sky Bet League Two |
| 12 | Fri 9 Feb | 33-1 v Notts CountyNotts County 1-3 Gillingham | Sky Bet League Two |
| 13 | Tue 13 Feb | 32-2 v Swindon TownGillingham 2-2 Swindon Town | Sky Bet League Two |
| 14 | Sat 17 Feb | 30-1 v Newport CountyNewport County 1-0 Gillingham | Sky Bet League Two |
| 15 | Tue 20 Feb | 30-0 v Stockport CountyGillingham 0-0 Stockport County | Sky Bet League Two |
| 16 | Sat 24 Feb | 31-0 v WrexhamGillingham 1-0 Wrexham | Sky Bet League Two |
| 17 | Sat 2 Mar | 32-0 v Salford CitySalford City 0-2 Gillingham | Sky Bet League Two |
| 18 | Tue 5 Mar | 30-2 v BarrowBarrow 2-0 Gillingham | Sky Bet League Two |
| 19 | Sat 9 Mar | 31-1 v Tranmere RoversGillingham 1-1 Tranmere Rovers | Sky Bet League Two |
| 20 | Tue 12 Mar | 3 0-2 v AFC WimbledonAFC Wimbledon 2-0 Gillingham | Sky Bet League Two |
| 21 | Sat 16 Mar | 31-1 v Grimsby TownGillingham 1-1 Grimsby Town | Sky Bet League Two |
| 22 | Sat 23 Mar | 33-2 v MorecambeMorecambe 2-3 Gillingham | Sky Bet League Two |
| 23 | Fri 29 Mar | 30-0 v Crewe AlexandraGillingham 0-0 Crewe Alexandra | Sky Bet League Two |
| 24 | Mon 1 Apr | 31-5 v Harrogate TownHarrogate Town 5-1 Gillingham | Sky Bet League Two |
| 25 | Sat 13 Apr | 33-0 v BarrowGillingham 3-0 Barrow | Sky Bet League Two |
| 26 | Sat 20 Apr | 31-2 v Mansfield TownMansfield Town 2-1 Gillingham | Sky Bet League Two |
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