| 1 | Tue 10 Jul 2018 | 25-1 v BromleyBromley 1-5 Gillingham | Friendly |
| 2 | Tue 24 Jul 2018 | 24-0 v EastleighEastleigh 0-4 Gillingham | Friendly |
| 3 | Tue 24 Jul 2018 | 24-0 v Chatham TownChatham Town 0-4 Gillingham | Friendly |
| 4 | Sat 4 Aug 2018 | 22-0 v Accrington StanleyAccrington Stanley 0-2 Gillingham | Sky Bet League One |
| 5 | Sat 11 Aug 2018 | 2 3-1 v Burton AlbionGillingham 3-1 Burton Albion | Sky Bet League One |
| 6 | Tue 14 Aug 2018 | 20-0 v MillwallMillwall 0-0 Gillingham | Carabao Cup First Round |
| 7 | Sat 18 Aug 2018 | 2 1-2 v WalsallWalsall 2-1 Gillingham | Sky Bet League One |
| 8 | Wed 22 Aug 2018 | 21-4 v SunderlandGillingham 1-4 Sunderland | Sky Bet League One |
| 9 | Sat 25 Aug 2018 | 2 1-1 v Coventry CityGillingham 1-1 Coventry City | Sky Bet League One |
| 10 | Tue 4 Sep 2018 | 20-4 v PortsmouthPortsmouth 4-0 Gillingham | Checkatrade Trophy Southern Group A |
| 11 | Sat 8 Sep 2018 | 20-1 v AFC WimbledonGillingham 0-1 AFC Wimbledon | Sky Bet League One |
| 12 | Sat 15 Sep 2018 | 20-3 v RochdaleRochdale 3-0 Gillingham | Sky Bet League One |
| 13 | Sat 29 Sep 2018 | 22-2 v Shrewsbury TownShrewsbury Town 2-2 Gillingham | Sky Bet League One |
| 14 | Sat 6 Oct 2018 | 22-0 v PortsmouthPortsmouth 0-2 Gillingham | Sky Bet League One |
| 15 | Sat 13 Oct 2018 | 20-2 v Southend UnitedGillingham 0-2 Southend United | Sky Bet League One |
| 16 | Sat 20 Oct 2018 | 23-3 v Doncaster RoversDoncaster Rovers 3-3 Gillingham | Sky Bet League One |
| 17 | Tue 23 Oct 2018 | 21-3 v Plymouth ArgylePlymouth Argyle 3-1 Gillingham | Sky Bet League One |
| 18 | Sat 27 Oct 2018 | 24-0 v Bradford CityGillingham 4-0 Bradford City | Sky Bet League One |
| 19 | Sat 3 Nov 2018 | 23-0 v Fleetwood TownGillingham 3-0 Fleetwood Town | Sky Bet League One |
| 20 | Tue 6 Nov 2018 | 2 0-1 v BlackpoolGillingham 0-1 Blackpool | Sky Bet League One |
| 21 | Sat 10 Nov 2018 | 20-0 v Hartlepool UnitedGillingham 0-0 Hartlepool United | Emirates FA Cup First Round |
| 22 | Sat 17 Nov 2018 | 20-1 v Oxford UnitedOxford United 1-0 Gillingham | Sky Bet League One |
| 23 | Wed 21 Nov 2018 | 24-3 v Hartlepool UnitedHartlepool United 3-4 Gillingham | Emirates FA Cup First Round Replay |
| 24 | Sat 24 Nov 2018 | 21-3 v Luton TownGillingham 1-3 Luton Town | Sky Bet League One |
| 25 | Tue 27 Nov 2018 | 22-1 v Bristol RoversBristol Rovers 1-2 Gillingham | Sky Bet League One |
| 26 | Sun 2 Dec 2018 | 21-0 v Slough TownSlough Town 0-1 Gillingham | Emirates FA Cup Second Round |
| 27 | Sat 22 Dec 2018 | 20-2 v Charlton AthleticCharlton Athletic 2-0 Gillingham | Sky Bet League One |
| 28 | Wed 26 Dec 2018 | 22-0 v PortsmouthGillingham 2-0 Portsmouth | Sky Bet League One |
| 29 | Sat 29 Dec 2018 | 21-3 v Doncaster RoversGillingham 1-3 Doncaster Rovers | Sky Bet League One |
| 30 | Tue 1 Jan 2019 | 20-2 v Southend UnitedSouthend United 2-0 Gillingham | Sky Bet League One |
| 31 | Sat 5 Jan 2019 | 21-0 v Cardiff CityGillingham 1-0 Cardiff City | Emirates FA Cup Third Round |
| 32 | Sat 12 Jan 2019 | 23-2 v Burton AlbionBurton Albion 2-3 Gillingham | Sky Bet League One |
| 33 | Sat 19 Jan 2019 | 20-3 v WalsallGillingham 0-3 Walsall | Sky Bet League One |
| 34 | Sat 26 Jan 2019 | 21-4 v Swansea CitySwansea City 4-1 Gillingham | Emirates FA Cup Fourth Round |
| 35 | Sat 16 Feb 2019 | 21-0 v Scunthorpe UnitedGillingham 1-0 Scunthorpe United | Sky Bet League One |
| 36 | Tue 19 Feb 2019 | 22-4 v SunderlandSunderland 4-2 Gillingham | Sky Bet League One |
| 37 | Sat 23 Feb 2019 | 21-0 v Wycombe WanderersWycombe Wanderers 0-1 Gillingham | Sky Bet League One |
| 38 | Sat 2 Mar 2019 | 21-1 v Fleetwood TownFleetwood Town 1-1 Gillingham | Sky Bet League One |
| 39 | Sat 9 Mar 2019 | 2 1-0 v Oxford UnitedGillingham 1-0 Oxford United | Sky Bet League One |
| 40 | Tue 12 Mar 2019 | 20-1 v Bristol RoversGillingham 0-1 Bristol Rovers | Sky Bet League One |
| 41 | Sat 16 Mar 2019 | 22-2 v Luton TownLuton Town 2-2 Gillingham | Sky Bet League One |
| 42 | Sat 23 Mar 2019 | 24-2 v AFC WimbledonAFC Wimbledon 2-4 Gillingham | Sky Bet League One |
| 43 | Sat 30 Mar 2019 | 21-1 v RochdaleGillingham 1-1 Rochdale | Sky Bet League One |
| 44 | Sat 6 Apr 2019 | 2 0-2 v Peterborough UnitedPeterborough United 2-0 Gillingham | Sky Bet League One |
| 45 | Sat 13 Apr 2019 | 20-2 v Shrewsbury TownGillingham 0-2 Shrewsbury Town | Sky Bet League One |
| 46 | Fri 19 Apr 2019 | 23-1 v Plymouth ArgyleGillingham 3-1 Plymouth Argyle | Sky Bet League One |
| 47 | Mon 22 Apr 2019 | 21-1 v Bradford CityBradford City 1-1 Gillingham | Sky Bet League One |
| 48 | Sat 27 Apr 2019 | 2 0-2 v Charlton AthleticGillingham 0-2 Charlton Athletic | Sky Bet League One |
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