| 1 | Sat 5 Sep 2020 | 2 1-0 v Southend UnitedGillingham 1-0 Southend United | Carabao Cup First Round South |
| 2 | Tue 15 Sep 2020 | 21-1 v Coventry CityGillingham 1-1 Coventry City | Carabao Cup Second Round |
| 3 | Sat 19 Sep 2020 | 23-2 v Wigan AthleticWigan Athletic 2-3 Gillingham | Sky Bet League One |
| 4 | Wed 23 Sep 2020 | 2 0-1 v Stoke CityStoke City 1-0 Gillingham | Carabao Cup Third Round |
| 5 | Sat 26 Sep 2020 | 22-0 v BlackpoolGillingham 2-0 Blackpool | Sky Bet League One |
| 6 | Sat 3 Oct 2020 | 21-1 v Shrewsbury TownShrewsbury Town 1-1 Gillingham | Sky Bet League One |
| 7 | Sat 10 Oct 2020 | 23-1 v Oxford UnitedGillingham 3-1 Oxford United | Sky Bet League One |
| 8 | Sat 17 Oct 2020 | 20-2 v Milton Keynes DonsMilton Keynes Dons 2-0 Gillingham | Sky Bet League One |
| 9 | Tue 20 Oct 2020 | 20-2 v PortsmouthGillingham 0-2 Portsmouth | Sky Bet League One |
| 10 | Sat 24 Oct 2020 | 20-2 v Fleetwood TownGillingham 0-2 Fleetwood Town | Sky Bet League One |
| 11 | Tue 27 Oct 2020 | 20-1 v Ipswich TownIpswich Town 1-0 Gillingham | Sky Bet League One |
| 12 | Sat 31 Oct 2020 | 2 0-2 v SunderlandGillingham 0-2 Sunderland | Sky Bet League One |
| 13 | Tue 3 Nov 2020 | 21-0 v Crewe AlexandraCrewe Alexandra 0-1 Gillingham | Sky Bet League One |
| 14 | Sat 21 Nov 2020 | 21-1 v Charlton AthleticGillingham 1-1 Charlton Athletic | Sky Bet League One |
| 15 | Tue 24 Nov 2020 | 22-1 v AFC WimbledonGillingham 2-1 AFC Wimbledon | Sky Bet League One |
| 16 | Wed 2 Dec 2020 | 22-0 v Bristol RoversBristol Rovers 0-2 Gillingham | Sky Bet League One |
| 17 | Sat 5 Dec 2020 | 22-0 v Swindon TownGillingham 2-0 Swindon Town | Sky Bet League One |
| 18 | Tue 8 Dec 2020 | 20-2 v Cambridge UnitedCambridge United 2-0 Gillingham | Papa John’s Trophy Second Round |
| 19 | Sat 12 Dec 2020 | 21-2 v Doncaster RoversDoncaster Rovers 2-1 Gillingham | Sky Bet League One |
| 20 | Tue 15 Dec 2020 | 20-2 v Accrington StanleyGillingham 0-2 Accrington Stanley | Sky Bet League One |
| 21 | Sat 19 Dec 2020 | 24-1 v RochdaleRochdale 1-4 Gillingham | Sky Bet League One |
| 22 | Tue 29 Dec 2020 | 21-3 v Northampton TownNorthampton Town 3-1 Gillingham | Sky Bet League One |
| 23 | Sat 2 Jan 2021 | 2 0-1 v Plymouth ArgylePlymouth Argyle 1-0 Gillingham | Sky Bet League One |
| 24 | Sat 9 Jan 2021 | 20-1 v Burton AlbionGillingham 0-1 Burton Albion | Sky Bet League One |
| 25 | Sat 16 Jan 2021 | 2 1-0 v Accrington StanleyAccrington Stanley 0-1 Gillingham | Sky Bet League One |
| 26 | Sat 23 Jan 2021 | 22-2 v RochdaleGillingham 2-2 Rochdale | Sky Bet League One |
| 27 | Tue 26 Jan 2021 | 24-1 v Crewe AlexandraGillingham 4-1 Crewe Alexandra | Sky Bet League One |
| 28 | Sat 30 Jan 2021 | 22-2 v SunderlandSunderland 2-2 Gillingham | Sky Bet League One |
| 29 | Fri 5 Feb 2021 | 20-3 v Lincoln CityGillingham 0-3 Lincoln City | Sky Bet League One |
| 30 | Sat 13 Feb 2021 | 23-2 v Charlton AthleticCharlton Athletic 2-3 Gillingham | Sky Bet League One |
| 31 | Tue 16 Feb 2021 | 21-3 v Peterborough UnitedGillingham 1-3 Peterborough United | Sky Bet League One |
| 32 | Sat 20 Feb 2021 | 22-0 v Bristol RoversGillingham 2-0 Bristol Rovers | Sky Bet League One |
| 33 | Tue 23 Feb 2021 | 20-1 v AFC WimbledonAFC Wimbledon 1-0 Gillingham | Sky Bet League One |
| 34 | Sat 27 Feb 2021 | 21-1 v PortsmouthPortsmouth 1-1 Gillingham | Sky Bet League One |
| 35 | Tue 2 Mar 2021 | 23-2 v Milton Keynes DonsGillingham 3-2 Milton Keynes Dons | Sky Bet League One |
| 36 | Sat 6 Mar 2021 | 23-1 v Ipswich TownGillingham 3-1 Ipswich Town | Sky Bet League One |
| 37 | Tue 9 Mar 2021 | 20-1 v Fleetwood TownFleetwood Town 1-0 Gillingham | Sky Bet League One |
| 38 | Sat 13 Mar 2021 | 23-1 v Swindon TownSwindon Town 1-3 Gillingham | Sky Bet League One |
| 39 | Tue 16 Mar 2021 | 23-0 v Lincoln CityLincoln City 0-3 Gillingham | Sky Bet League One |
| 40 | Sat 20 Mar 2021 | 22-2 v Doncaster RoversGillingham 2-2 Doncaster Rovers | Sky Bet League One |
| 41 | Sat 27 Mar 2021 | 21-1 v Hull CityHull City 1-1 Gillingham | Sky Bet League One |
| 42 | Wed 31 Mar 2021 | 21-0 v Wigan AthleticGillingham 1-0 Wigan Athletic | Sky Bet League One |
| 43 | Mon 5 Apr 2021 | 21-4 v BlackpoolBlackpool 4-1 Gillingham | Sky Bet League One |
| 44 | Sat 10 Apr 2021 | 2 0-0 v Shrewsbury TownGillingham 0-0 Shrewsbury Town | Sky Bet League One |
| 45 | Sat 17 Apr 2021 | 2 2-3 v Oxford UnitedOxford United 3-2 Gillingham | Sky Bet League One |
| 46 | Tue 20 Apr 2021 | 21-0 v Peterborough UnitedPeterborough United 0-1 Gillingham | Sky Bet League One |
| 47 | Sat 24 Apr 2021 | 22-2 v Northampton TownGillingham 2-2 Northampton Town | Sky Bet League One |
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