| 1 | Sat 26 Aug | 40-3 v Colchester UnitedGillingham 0-3 Colchester United | Sky Bet League Two |
| 2 | Tue 29 Aug | 42-3 v Luton TownLuton Town 3-2 Gillingham | Carabao Cup Second Round |
| 3 | Sat 2 Sep | 40-2 v Grimsby TownGrimsby Town 2-0 Gillingham | Sky Bet League Two |
| 4 | Tue 5 Sep | 42-1 v Leyton OrientGillingham 2-1 Leyton Orient | EFL Trophy |
| 5 | Sat 9 Sep | 23 1-0 v Harrogate TownGillingham 1-0 Harrogate Town | Sky Bet League Two |
| 6 | Sat 16 Sep | 42-1 v MorecambeGillingham 2-1 Morecambe | Sky Bet League Two |
| 7 | Sat 23 Sep | 41-2 v Doncaster RoversDoncaster Rovers 2-1 Gillingham | Sky Bet League Two |
| 8 | Sat 30 Sep | 41-1 v Mansfield TownGillingham 1-1 Mansfield Town | Sky Bet League Two |
| 9 | Tue 3 Oct | 40-2 v Crewe AlexandraCrewe Alexandra 2-0 Gillingham | Sky Bet League Two |
| 10 | Sat 7 Oct | 42-1 v Milton Keynes DonsGillingham 2-1 Milton Keynes Dons | Sky Bet League Two |
| 11 | Tue 10 Oct | 41-5 v PortsmouthPortsmouth 5-1 Gillingham | EFL Trophy |
| 12 | Sat 14 Oct | 41-4 v WalsallWalsall 4-1 Gillingham | Sky Bet League Two |
| 13 | Sat 21 Oct | 41-2 v Notts CountyGillingham 1-2 Notts County | Sky Bet League Two |
| 14 | Tue 24 Oct | 41-0 v Swindon TownSwindon Town 0-1 Gillingham | Sky Bet League Two |
| 15 | Sat 28 Oct | 40-2 v Newport CountyGillingham 0-2 Newport County | Sky Bet League Two |
| 16 | Sat 4 Nov | 42-0 v HerefordHereford 0-2 Gillingham | Emirates FA Cup First Round |
| 17 | Sat 11 Nov | 40-2 v WrexhamWrexham 2-0 Gillingham | Sky Bet League Two |
| 18 | Sat 18 Nov | 43-1 v Salford CityGillingham 3-1 Salford City | Sky Bet League Two |
| 19 | Sat 25 Nov | 4 1-3 v Tranmere RoversTranmere Rovers 3-1 Gillingham | Sky Bet League Two |
| 20 | Tue 28 Nov | 41-0 v AFC WimbledonGillingham 1-0 AFC Wimbledon | Sky Bet League Two |
| 21 | Sat 2 Dec | 42-0 v Charlton AthleticGillingham 2-0 Charlton Athletic | Emirates FA Cup Second Round |
| 22 | Sat 16 Dec | 4 0-2 v Bradford CityGillingham 0-2 Bradford City | Sky Bet League Two |
| 23 | Fri 22 Dec | 40-0 v Forest Green RoversForest Green Rovers 0-0 Gillingham | Sky Bet League Two |
| 24 | Tue 26 Dec | 40-2 v Crawley TownGillingham 0-2 Crawley Town | Sky Bet League Two |
| 25 | Fri 29 Dec | 41-0 v Sutton UnitedGillingham 1-0 Sutton United | Sky Bet League Two |
| 26 | Mon 1 Jan | 41-0 v Colchester UnitedColchester United 0-1 Gillingham | Sky Bet League Two |
| 27 | Sat 6 Jan | 40-4 v Sheffield UnitedGillingham 0-4 Sheffield United | Emirates FA Cup Third Round |
| 28 | Sat 13 Jan | 42-1 v Accrington StanleyAccrington Stanley 1-2 Gillingham | Sky Bet League Two |
| 29 | Sat 20 Jan | 41-1 v Forest Green RoversGillingham 1-1 Forest Green Rovers | Sky Bet League Two |
| 30 | Sat 27 Jan | 41-2 v Milton Keynes DonsMilton Keynes Dons 2-1 Gillingham | Sky Bet League Two |
| 31 | Sat 3 Feb | 41-1 v WalsallGillingham 1-1 Walsall | Sky Bet League Two |
| 32 | Fri 9 Feb | 43-1 v Notts CountyNotts County 1-3 Gillingham | Sky Bet League Two |
| 33 | Tue 13 Feb | 42-2 v Swindon TownGillingham 2-2 Swindon Town | Sky Bet League Two |
| 34 | Sat 17 Feb | 4 0-1 v Newport CountyNewport County 1-0 Gillingham | Sky Bet League Two |
| 35 | Tue 20 Feb | 40-0 v Stockport CountyGillingham 0-0 Stockport County | Sky Bet League Two |
| 36 | Sat 24 Feb | 41-0 v WrexhamGillingham 1-0 Wrexham | Sky Bet League Two |
| 37 | Sat 2 Mar | 4 2-0 v Salford CitySalford City 0-2 Gillingham | Sky Bet League Two |
| 38 | Tue 5 Mar | 4 0-2 v BarrowBarrow 2-0 Gillingham | Sky Bet League Two |
| 39 | Sat 9 Mar | 41-1 v Tranmere RoversGillingham 1-1 Tranmere Rovers | Sky Bet League Two |
| 40 | Tue 12 Mar | 4 0-2 v AFC WimbledonAFC Wimbledon 2-0 Gillingham | Sky Bet League Two |
| 41 | Fri 29 Mar | 40-0 v Crewe AlexandraGillingham 0-0 Crewe Alexandra | Sky Bet League Two |
| 42 | Mon 1 Apr | 41-5 v Harrogate TownHarrogate Town 5-1 Gillingham | Sky Bet League Two |
| 43 | Sat 6 Apr | 40-1 v Bradford CityBradford City 1-0 Gillingham | Sky Bet League Two |
| 44 | Sat 13 Apr | 43-0 v BarrowGillingham 3-0 Barrow | Sky Bet League Two |
| 45 | Sat 20 Apr | 41-2 v Mansfield TownMansfield Town 2-1 Gillingham | Sky Bet League Two |
| 46 | Sat 27 Apr | 42-2 v Doncaster RoversGillingham 2-2 Doncaster Rovers | Sky Bet League Two |
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