| 1 | Sat 10 Aug | 11 4-1 v Carlisle UnitedGillingham 4-1 Carlisle United | Sky Bet League Two |
| 2 | Tue 13 Aug | 111-3 v Swansea CitySwansea City 3-1 Gillingham | Carabao Cup First Round |
| 3 | Sat 24 Aug | 11 0-0 v Fleetwood TownFleetwood Town 0-0 Gillingham | Sky Bet League Two |
| 4 | Sat 31 Aug | 111-0 v ChesterfieldGillingham 1-0 Chesterfield | Sky Bet League Two |
| 5 | Sat 14 Dec | 11 1-0 v Milton Keynes DonsMilton Keynes Dons 0-1 Gillingham | Sky Bet League Two |
| 6 | Fri 20 Dec | 112-2 v Cheltenham TownGillingham 2-2 Cheltenham Town | Sky Bet League Two |
| 7 | Thu 26 Dec | 110-2 v Colchester UnitedColchester United 2-0 Gillingham | Sky Bet League Two |
| 8 | Mon 30 Dec | 110-1 v AFC WimbledonAFC Wimbledon 1-0 Gillingham | Sky Bet League Two |
| 9 | Sat 18 Jan | 110-1 v Doncaster RoversGillingham 0-1 Doncaster Rovers | Sky Bet League Two |
| 10 | Sat 1 Feb | 111-2 v Notts CountyGillingham 1-2 Notts County | Sky Bet League Two |
| 11 | Tue 1 Apr | 111-1 v Colchester UnitedGillingham 1-1 Colchester United | Sky Bet League Two |
| 12 | Tue 8 Apr | 11 1-1 v ChesterfieldChesterfield 1-1 Gillingham | Sky Bet League Two |
| 13 | Sat 12 Apr | 111-0 v Milton Keynes DonsGillingham 1-0 Milton Keynes Dons | Sky Bet League Two |
| 14 | Fri 18 Apr | 111-1 v Cheltenham TownCheltenham Town 1-1 Gillingham | Sky Bet League Two |
| 15 | Mon 21 Apr | 11 1-0 v AFC WimbledonGillingham 1-0 AFC Wimbledon | Sky Bet League Two |
| 16 | Sat 26 Apr | 111-1 v Swindon TownGillingham 1-1 Swindon Town | Sky Bet League Two |
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