| 1 | Sat 5 Sep 2020 | 161-0 v Southend UnitedGillingham 1-0 Southend United | Carabao Cup First Round South |
| 2 | Tue 15 Sep 2020 | 161-1 v Coventry CityGillingham 1-1 Coventry City | Carabao Cup Second Round |
| 3 | Wed 23 Sep 2020 | 160-1 v Stoke CityStoke City 1-0 Gillingham | Carabao Cup Third Round |
| 4 | Tue 6 Oct 2020 | 160-2 v Ipswich TownIpswich Town 2-0 Gillingham | Papa John’s Trophy Group 9 |
| 5 | Sat 10 Oct 2020 | 163-1 v Oxford UnitedGillingham 3-1 Oxford United | Sky Bet League One |
| 6 | Tue 20 Oct 2020 | 160-2 v PortsmouthGillingham 0-2 Portsmouth | Sky Bet League One |
| 7 | Sat 24 Oct 2020 | 160-2 v Fleetwood TownGillingham 0-2 Fleetwood Town | Sky Bet League One |
| 8 | Tue 27 Oct 2020 | 16 0-1 v Ipswich TownIpswich Town 1-0 Gillingham | Sky Bet League One |
| 9 | Sat 31 Oct 2020 | 16 0-2 v SunderlandGillingham 0-2 Sunderland | Sky Bet League One |
| 10 | Tue 24 Nov 2020 | 162-1 v AFC WimbledonGillingham 2-1 AFC Wimbledon | Sky Bet League One |
| 11 | Sat 5 Dec 2020 | 162-0 v Swindon TownGillingham 2-0 Swindon Town | Sky Bet League One |
| 12 | Tue 8 Dec 2020 | 160-2 v Cambridge UnitedCambridge United 2-0 Gillingham | Papa John’s Trophy Second Round |
| 13 | Sat 12 Dec 2020 | 161-2 v Doncaster RoversDoncaster Rovers 2-1 Gillingham | Sky Bet League One |
| 14 | Tue 15 Dec 2020 | 160-2 v Accrington StanleyGillingham 0-2 Accrington Stanley | Sky Bet League One |
| 15 | Sat 19 Dec 2020 | 164-1 v RochdaleRochdale 1-4 Gillingham | Sky Bet League One |
| 16 | Tue 29 Dec 2020 | 161-3 v Northampton TownNorthampton Town 3-1 Gillingham | Sky Bet League One |
| 17 | Sat 2 Jan 2021 | 160-1 v Plymouth ArgylePlymouth Argyle 1-0 Gillingham | Sky Bet League One |
| 18 | Sat 9 Jan 2021 | 160-1 v Burton AlbionGillingham 0-1 Burton Albion | Sky Bet League One |
| 19 | Sat 16 Jan 2021 | 161-0 v Accrington StanleyAccrington Stanley 0-1 Gillingham | Sky Bet League One |
| 20 | Sat 23 Jan 2021 | 162-2 v RochdaleGillingham 2-2 Rochdale | Sky Bet League One |
| 21 | Tue 26 Jan 2021 | 164-1 v Crewe AlexandraGillingham 4-1 Crewe Alexandra | Sky Bet League One |
| 22 | Sat 30 Jan 2021 | 162-2 v SunderlandSunderland 2-2 Gillingham | Sky Bet League One |
| 23 | Fri 5 Feb 2021 | 160-3 v Lincoln CityGillingham 0-3 Lincoln City | Sky Bet League One |
| 24 | Sat 13 Feb 2021 | 163-2 v Charlton AthleticCharlton Athletic 2-3 Gillingham | Sky Bet League One |
| 25 | Tue 16 Feb 2021 | 161-3 v Peterborough UnitedGillingham 1-3 Peterborough United | Sky Bet League One |
| 26 | Sat 20 Feb 2021 | 162-0 v Bristol RoversGillingham 2-0 Bristol Rovers | Sky Bet League One |
| 27 | Sat 6 Mar 2021 | 163-1 v Ipswich TownGillingham 3-1 Ipswich Town | Sky Bet League One |
| 28 | Tue 9 Mar 2021 | 160-1 v Fleetwood TownFleetwood Town 1-0 Gillingham | Sky Bet League One |
| 29 | Sat 13 Mar 2021 | 163-1 v Swindon TownSwindon Town 1-3 Gillingham | Sky Bet League One |
| 30 | Tue 16 Mar 2021 | 163-0 v Lincoln CityLincoln City 0-3 Gillingham | Sky Bet League One |
| 31 | Sat 20 Mar 2021 | 162-2 v Doncaster RoversGillingham 2-2 Doncaster Rovers | Sky Bet League One |
| 32 | Sat 27 Mar 2021 | 16 1-1 v Hull CityHull City 1-1 Gillingham | Sky Bet League One |
| 33 | Wed 31 Mar 2021 | 161-0 v Wigan AthleticGillingham 1-0 Wigan Athletic | Sky Bet League One |
| 34 | Mon 5 Apr 2021 | 161-4 v BlackpoolBlackpool 4-1 Gillingham | Sky Bet League One |
| 35 | Sat 10 Apr 2021 | 160-0 v Shrewsbury TownGillingham 0-0 Shrewsbury Town | Sky Bet League One |
| 36 | Sat 17 Apr 2021 | 162-3 v Oxford UnitedOxford United 3-2 Gillingham | Sky Bet League One |
| 37 | Tue 20 Apr 2021 | 16 1-0 v Peterborough UnitedPeterborough United 0-1 Gillingham | Sky Bet League One |
| 38 | Sat 24 Apr 2021 | 162-2 v Northampton TownGillingham 2-2 Northampton Town | Sky Bet League One |
| 39 | Sat 1 May 2021 | 16 1-1 v Burton AlbionBurton Albion 1-1 Gillingham | Sky Bet League One |
| 40 | Sun 9 May 2021 | 161-0 v Plymouth ArgyleGillingham 1-0 Plymouth Argyle | Sky Bet League One |
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