| 1 | Tue 24 Jul 2018 | 44-0 v EastleighEastleigh 0-4 Gillingham | Friendly |
| 2 | Tue 24 Jul 2018 | 44-0 v Chatham TownChatham Town 0-4 Gillingham | Friendly |
| 3 | Tue 14 Aug 2018 | 40-0 v MillwallMillwall 0-0 Gillingham | Carabao Cup First Round |
| 4 | Sat 1 Sep 2018 | 41-2 v BarnsleyBarnsley 2-1 Gillingham | Sky Bet League One |
| 5 | Tue 4 Sep 2018 | 40-4 v PortsmouthPortsmouth 4-0 Gillingham | Checkatrade Trophy Southern Group A |
| 6 | Sat 8 Sep 2018 | 40-1 v AFC WimbledonGillingham 0-1 AFC Wimbledon | Sky Bet League One |
| 7 | Sat 15 Sep 2018 | 40-3 v RochdaleRochdale 3-0 Gillingham | Sky Bet League One |
| 8 | Sat 29 Sep 2018 | 4 2-2 v Shrewsbury TownShrewsbury Town 2-2 Gillingham | Sky Bet League One |
| 9 | Sat 6 Oct 2018 | 42-0 v PortsmouthPortsmouth 0-2 Gillingham | Sky Bet League One |
| 10 | Sat 13 Oct 2018 | 40-2 v Southend UnitedGillingham 0-2 Southend United | Sky Bet League One |
| 11 | Sat 20 Oct 2018 | 43-3 v Doncaster RoversDoncaster Rovers 3-3 Gillingham | Sky Bet League One |
| 12 | Tue 13 Nov 2018 | 42-1 v Crawley TownGillingham 2-1 Crawley Town | Checkatrade Trophy Southern Group A |
| 13 | Wed 21 Nov 2018 | 44-3 v Hartlepool UnitedHartlepool United 3-4 Gillingham | Emirates FA Cup First Round Replay |
| 14 | Sat 8 Dec 2018 | 42-0 v Scunthorpe UnitedScunthorpe United 0-2 Gillingham | Sky Bet League One |
| 15 | Sat 15 Dec 2018 | 42-2 v Wycombe WanderersGillingham 2-2 Wycombe Wanderers | Sky Bet League One |
| 16 | Sat 22 Dec 2018 | 40-2 v Charlton AthleticCharlton Athletic 2-0 Gillingham | Sky Bet League One |
| 17 | Wed 26 Dec 2018 | 42-0 v PortsmouthGillingham 2-0 Portsmouth | Sky Bet League One |
| 18 | Sat 29 Dec 2018 | 41-3 v Doncaster RoversGillingham 1-3 Doncaster Rovers | Sky Bet League One |
| 19 | Tue 1 Jan 2019 | 4 0-2 v Southend UnitedSouthend United 2-0 Gillingham | Sky Bet League One |
| 20 | Sat 5 Jan 2019 | 41-0 v Cardiff CityGillingham 1-0 Cardiff City | Emirates FA Cup Third Round |
| 21 | Sat 12 Jan 2019 | 43-2 v Burton AlbionBurton Albion 2-3 Gillingham | Sky Bet League One |
| 22 | Sat 19 Jan 2019 | 40-3 v WalsallGillingham 0-3 Walsall | Sky Bet League One |
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