| 1 | Sat 2 Aug | 101-1 v Accrington StanleyAccrington Stanley 1-1 Gillingham | Sky Bet League Two |
| 2 | Tue 12 Aug | 101-1 v AFC WimbledonGillingham 1-1 AFC Wimbledon | Carabao Cup First Round |
| 3 | Sat 16 Aug | 101-1 v Tranmere RoversTranmere Rovers 1-1 Gillingham | Sky Bet League Two |
| 4 | Tue 19 Aug | 104-1 v ChesterfieldGillingham 4-1 Chesterfield | Sky Bet League Two |
| 5 | Sat 23 Aug | 101-0 v Crewe AlexandraGillingham 1-0 Crewe Alexandra | Sky Bet League Two |
| 6 | Sat 6 Sep | 102-2 v BromleyBromley 2-2 Gillingham | Sky Bet League Two |
| 7 | Sat 13 Sep | 101-0 v Notts CountyGillingham 1-0 Notts County | Sky Bet League Two |
| 8 | Sat 20 Sep | 103-1 v Newport CountyNewport County 1-3 Gillingham | Sky Bet League Two |
| 9 | Sat 27 Sep | 100-1 v Harrogate TownGillingham 0-1 Harrogate Town | Sky Bet League Two |
| 10 | Sat 4 Oct | 102-3 v Milton Keynes DonsMilton Keynes Dons 3-2 Gillingham | Sky Bet League Two |
| 11 | Sat 11 Oct | 101-1 v Cheltenham TownGillingham 1-1 Cheltenham Town | Sky Bet League Two |
| 12 | Sat 18 Oct | 10 0-1 v Grimsby TownGrimsby Town 1-0 Gillingham | Sky Bet League Two |
| 13 | Sat 15 Nov | 102-2 v Crawley TownGillingham 2-2 Crawley Town | Sky Bet League Two |
| 14 | Sat 22 Nov | 10 1-1 v BarnetGillingham 1-1 Barnet | Sky Bet League Two |
| 15 | Sat 29 Nov | 103-3 v Shrewsbury TownShrewsbury Town 3-3 Gillingham | Sky Bet League Two |
| 16 | Sat 6 Dec | 100-0 v Colchester UnitedColchester United 0-0 Gillingham | Sky Bet League Two |
| 17 | Sat 13 Dec | 102-2 v BarrowGillingham 2-2 Barrow | Sky Bet League Two |
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