| 1 | Sat 10 Aug | 44-1 v Carlisle UnitedGillingham 4-1 Carlisle United | Sky Bet League Two |
| 2 | Sat 19 Oct | 41-2 v Bradford CityBradford City 2-1 Gillingham | Sky Bet League Two |
| 3 | Tue 22 Oct | 40-2 v Newport CountyGillingham 0-2 Newport County | Sky Bet League Two |
| 4 | Sat 2 Nov | 40-2 v BlackpoolGillingham 0-2 Blackpool | Emirates FA Cup First Round |
| 5 | Sat 9 Nov | 41-0 v Port ValeGillingham 1-0 Port Vale | Sky Bet League Two |
| 6 | Tue 12 Nov | 41-1 v StevenageStevenage 1-1 Gillingham | EFL Trophy Southern Group D |
| 7 | Sat 23 Nov | 41-2 v Harrogate TownGillingham 1-2 Harrogate Town | Sky Bet League Two |
| 8 | Wed 4 Dec | 41-2 v BromleyBromley 2-1 Gillingham | Sky Bet League Two |
| 9 | Sat 7 Dec | 41-0 v Salford CityGillingham 1-0 Salford City | Sky Bet League Two |
| 10 | Sat 14 Dec | 41-0 v Milton Keynes DonsMilton Keynes Dons 0-1 Gillingham | Sky Bet League Two |
| 11 | Fri 20 Dec | 42-2 v Cheltenham TownGillingham 2-2 Cheltenham Town | Sky Bet League Two |
| 12 | Thu 26 Dec | 40-2 v Colchester UnitedColchester United 2-0 Gillingham | Sky Bet League Two |
| 13 | Mon 30 Dec | 40-1 v AFC WimbledonAFC Wimbledon 1-0 Gillingham | Sky Bet League Two |
| 14 | Sat 8 Mar | 4 1-0 v Bradford CityGillingham 1-0 Bradford City | Sky Bet League Two |
| 15 | Sat 15 Mar | 41-1 v Accrington StanleyAccrington Stanley 1-1 Gillingham | Sky Bet League Two |
| 16 | Sat 22 Mar | 40-0 v WalsallGillingham 0-0 Walsall | Sky Bet League Two |
| 17 | Sat 29 Mar | 4 1-1 v Harrogate TownHarrogate Town 1-1 Gillingham | Sky Bet League Two |
| 18 | Tue 1 Apr | 41-1 v Colchester UnitedGillingham 1-1 Colchester United | Sky Bet League Two |
| 19 | Sat 5 Apr | 42-2 v Salford CitySalford City 2-2 Gillingham | Sky Bet League Two |
| 20 | Tue 8 Apr | 41-1 v ChesterfieldChesterfield 1-1 Gillingham | Sky Bet League Two |
| 21 | Sat 12 Apr | 41-0 v Milton Keynes DonsGillingham 1-0 Milton Keynes Dons | Sky Bet League Two |
| 22 | Fri 18 Apr | 41-1 v Cheltenham TownCheltenham Town 1-1 Gillingham | Sky Bet League Two |
| 23 | Mon 21 Apr | 41-0 v AFC WimbledonGillingham 1-0 AFC Wimbledon | Sky Bet League Two |
| 24 | Sat 26 Apr | 41-1 v Swindon TownGillingham 1-1 Swindon Town | Sky Bet League Two |
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