| 1 | Sat 26 Aug | 140-3 v Colchester UnitedGillingham 0-3 Colchester United | Sky Bet League Two |
| 2 | Tue 29 Aug | 142-3 v Luton TownLuton Town 3-2 Gillingham | Carabao Cup Second Round |
| 3 | Sat 2 Sep | 140-2 v Grimsby TownGrimsby Town 2-0 Gillingham | Sky Bet League Two |
| 4 | Tue 5 Sep | 142-1 v Leyton OrientGillingham 2-1 Leyton Orient | EFL Trophy |
| 5 | Sat 9 Sep | 141-0 v Harrogate TownGillingham 1-0 Harrogate Town | Sky Bet League Two |
| 6 | Sat 16 Sep | 142-1 v MorecambeGillingham 2-1 Morecambe | Sky Bet League Two |
| 7 | Sat 23 Sep | 141-2 v Doncaster RoversDoncaster Rovers 2-1 Gillingham | Sky Bet League Two |
| 8 | Tue 3 Oct | 140-2 v Crewe AlexandraCrewe Alexandra 2-0 Gillingham | Sky Bet League Two |
| 9 | Sat 7 Oct | 142-1 v Milton Keynes DonsGillingham 2-1 Milton Keynes Dons | Sky Bet League Two |
| 10 | Sat 14 Oct | 141-4 v WalsallWalsall 4-1 Gillingham | Sky Bet League Two |
| 11 | Sat 2 Dec | 142-0 v Charlton AthleticGillingham 2-0 Charlton Athletic | Emirates FA Cup Second Round |
| 12 | Sat 16 Dec | 140-2 v Bradford CityGillingham 0-2 Bradford City | Sky Bet League Two |
| 13 | Fri 22 Dec | 140-0 v Forest Green RoversForest Green Rovers 0-0 Gillingham | Sky Bet League Two |
| 14 | Mon 1 Jan | 141-0 v Colchester UnitedColchester United 0-1 Gillingham | Sky Bet League Two |
| 15 | Sat 13 Jan | 142-1 v Accrington StanleyAccrington Stanley 1-2 Gillingham | Sky Bet League Two |
| 16 | Fri 9 Feb | 143-1 v Notts CountyNotts County 1-3 Gillingham | Sky Bet League Two |
| 17 | Tue 13 Feb | 142-2 v Swindon TownGillingham 2-2 Swindon Town | Sky Bet League Two |
| 18 | Sat 24 Feb | 141-0 v WrexhamGillingham 1-0 Wrexham | Sky Bet League Two |
| 19 | Sat 2 Mar | 142-0 v Salford CitySalford City 0-2 Gillingham | Sky Bet League Two |
| 20 | Tue 12 Mar | 140-2 v AFC WimbledonAFC Wimbledon 2-0 Gillingham | Sky Bet League Two |
| 21 | Sat 16 Mar | 14 1-1 v Grimsby TownGillingham 1-1 Grimsby Town | Sky Bet League Two |
| 22 | Sat 23 Mar | 143-2 v MorecambeMorecambe 2-3 Gillingham | Sky Bet League Two |
| 23 | Mon 1 Apr | 141-5 v Harrogate TownHarrogate Town 5-1 Gillingham | Sky Bet League Two |
| 24 | Sat 13 Apr | 143-0 v BarrowGillingham 3-0 Barrow | Sky Bet League Two |
| 25 | Sat 20 Apr | 141-2 v Mansfield TownMansfield Town 2-1 Gillingham | Sky Bet League Two |
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