| 1 | Tue 3 Sep | 201-2 v Peterborough UnitedGillingham 1-2 Peterborough United | EFL Trophy Southern Group D |
| 2 | Sat 7 Sep | 20 0-1 v Doncaster RoversDoncaster Rovers 1-0 Gillingham | Sky Bet League Two |
| 3 | Sat 14 Sep | 203-0 v Tranmere RoversGillingham 3-0 Tranmere Rovers | Sky Bet League Two |
| 4 | Sat 21 Sep | 201-0 v Notts CountyNotts County 0-1 Gillingham | Sky Bet League Two |
| 5 | Sat 28 Sep | 20 2-0 v BarrowGillingham 2-0 Barrow | Sky Bet League Two |
| 6 | Tue 1 Oct | 200-1 v Grimsby TownGillingham 0-1 Grimsby Town | Sky Bet League Two |
| 7 | Sat 5 Oct | 200-2 v Crewe AlexandraCrewe Alexandra 2-0 Gillingham | Sky Bet League Two |
| 8 | Sat 12 Oct | 201-2 v Accrington StanleyGillingham 1-2 Accrington Stanley | Sky Bet League Two |
| 9 | Sat 23 Nov | 201-2 v Harrogate TownGillingham 1-2 Harrogate Town | Sky Bet League Two |
| 10 | Wed 4 Dec | 201-2 v BromleyBromley 2-1 Gillingham | Sky Bet League Two |
| 11 | Sat 7 Dec | 201-0 v Salford CityGillingham 1-0 Salford City | Sky Bet League Two |
| 12 | Sat 14 Dec | 201-0 v Milton Keynes DonsMilton Keynes Dons 0-1 Gillingham | Sky Bet League Two |
| 13 | Fri 20 Dec | 202-2 v Cheltenham TownGillingham 2-2 Cheltenham Town | Sky Bet League Two |
| 14 | Thu 26 Dec | 200-2 v Colchester UnitedColchester United 2-0 Gillingham | Sky Bet League Two |
| 15 | Mon 30 Dec | 200-1 v AFC WimbledonAFC Wimbledon 1-0 Gillingham | Sky Bet League Two |
| 16 | Thu 2 Jan | 200-3 v BromleyGillingham 0-3 Bromley | Sky Bet League Two |
| 17 | Sat 18 Jan | 200-1 v Doncaster RoversGillingham 0-1 Doncaster Rovers | Sky Bet League Two |
| 18 | Sat 25 Jan | 201-1 v Tranmere RoversTranmere Rovers 1-1 Gillingham | Sky Bet League Two |
| 19 | Sat 1 Feb | 20 1-2 v Notts CountyGillingham 1-2 Notts County | Sky Bet League Two |
| 20 | Sat 8 Feb | 200-3 v BarrowBarrow 3-0 Gillingham | Sky Bet League Two |
| 21 | Tue 11 Feb | 201-1 v WalsallWalsall 1-1 Gillingham | Sky Bet League Two |
| 22 | Sat 15 Feb | 200-0 v Crewe AlexandraGillingham 0-0 Crewe Alexandra | Sky Bet League Two |
| 23 | Sat 22 Feb | 200-0 v Carlisle UnitedCarlisle United 0-0 Gillingham | Sky Bet League Two |
| 24 | Tue 25 Feb | 201-2 v Fleetwood TownGillingham 1-2 Fleetwood Town | Sky Bet League Two |
| 25 | Sat 1 Mar | 20 1-0 v MorecambeGillingham 1-0 Morecambe | Sky Bet League Two |
| 26 | Tue 4 Mar | 20 1-3 v Newport CountyNewport County 3-1 Gillingham | Sky Bet League Two |
| 27 | Sat 8 Mar | 20 1-0 v Bradford CityGillingham 1-0 Bradford City | Sky Bet League Two |
| 28 | Sat 15 Mar | 201-1 v Accrington StanleyAccrington Stanley 1-1 Gillingham | Sky Bet League Two |
| 29 | Sat 22 Mar | 200-0 v WalsallGillingham 0-0 Walsall | Sky Bet League Two |
| 30 | Sat 29 Mar | 201-1 v Harrogate TownHarrogate Town 1-1 Gillingham | Sky Bet League Two |
| 31 | Tue 1 Apr | 201-1 v Colchester UnitedGillingham 1-1 Colchester United | Sky Bet League Two |
| 32 | Sat 5 Apr | 20 2-2 v Salford CitySalford City 2-2 Gillingham | Sky Bet League Two |
| 33 | Tue 8 Apr | 201-1 v ChesterfieldChesterfield 1-1 Gillingham | Sky Bet League Two |
| 34 | Sat 12 Apr | 201-0 v Milton Keynes DonsGillingham 1-0 Milton Keynes Dons | Sky Bet League Two |
| 35 | Fri 18 Apr | 20 1-1 v Cheltenham TownCheltenham Town 1-1 Gillingham | Sky Bet League Two |
| 36 | Mon 21 Apr | 201-0 v AFC WimbledonGillingham 1-0 AFC Wimbledon | Sky Bet League Two |
| 37 | Sat 26 Apr | 201-1 v Swindon TownGillingham 1-1 Swindon Town | Sky Bet League Two |
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