| 1 | Sat 3 Aug 2019 | 51-1 v Doncaster RoversDoncaster Rovers 1-1 Gillingham |
| 2 | Sat 10 Aug 2019 | 51-2 v Burton AlbionGillingham 1-2 Burton Albion |
| 3 | Tue 20 Aug 2019 | 52-2 v BlackpoolGillingham 2-2 Blackpool |
| 4 | Sat 24 Aug 2019 | 50-1 v Coventry CityCoventry City 1-0 Gillingham |
| 5 | Sat 31 Aug 2019 | 55-0 v Bolton WanderersGillingham 5-0 Bolton Wanderers |
| 6 | Sat 14 Sep 2019 | 52-0 v Wycombe WanderersGillingham 2-0 Wycombe Wanderers |
| 7 | Tue 17 Sep 2019 | 51-1 v Bristol RoversBristol Rovers 1-1 Gillingham |
| 8 | Sat 21 Sep 2019 | 50-1 v Ipswich TownGillingham 0-1 Ipswich Town |
| 9 | Sat 28 Sep 2019 | 5 0-3 v Oxford UnitedOxford United 3-0 Gillingham |
| 10 | Sat 5 Oct 2019 | 53-1 v Southend UnitedGillingham 3-1 Southend United |
| 11 | Sat 12 Oct 2019 | 5 0-0 v PortsmouthPortsmouth 0-0 Gillingham |
| 12 | Sat 19 Oct 2019 | 5 1-2 v Peterborough UnitedGillingham 1-2 Peterborough United |
| 13 | Tue 22 Oct 2019 | 51-1 v Shrewsbury TownShrewsbury Town 1-1 Gillingham |
| 14 | Sat 26 Oct 2019 | 51-0 v Accrington StanleyAccrington Stanley 0-1 Gillingham |
| 15 | Sat 2 Nov 2019 | 50-3 v Rotherham UnitedGillingham 0-3 Rotherham United |
| 16 | Sat 16 Nov 2019 | 5 1-0 v Lincoln CityGillingham 1-0 Lincoln City |
| 17 | Sat 23 Nov 2019 | 50-1 v AFC WimbledonAFC Wimbledon 1-0 Gillingham |
| 18 | Sat 7 Dec 2019 | 51-0 v SunderlandGillingham 1-0 Sunderland |
| 19 | Sat 14 Dec 2019 | 5 1-1 v Fleetwood TownFleetwood Town 1-1 Gillingham |
| 20 | Sat 21 Dec 2019 | 53-1 v Milton Keynes DonsGillingham 3-1 Milton Keynes Dons |
| 21 | Thu 26 Dec 2019 | 50-0 v Ipswich TownIpswich Town 0-0 Gillingham |
| 22 | Sun 29 Dec 2019 | 51-0 v RochdaleGillingham 1-0 Rochdale |
| 23 | Wed 1 Jan 2020 | 51-1 v PortsmouthGillingham 1-1 Portsmouth |
| 24 | Sat 11 Jan 2020 | 50-0 v Peterborough UnitedPeterborough United 0-0 Gillingham |
| 25 | Sat 18 Jan 2020 | 51-1 v Oxford UnitedGillingham 1-1 Oxford United |
| 26 | Wed 29 Jan 2020 | 52-0 v Shrewsbury TownGillingham 2-0 Shrewsbury Town |
| 27 | Sat 8 Feb 2020 | 50-0 v Burton AlbionBurton Albion 0-0 Gillingham |
| 28 | Tue 11 Feb 2020 | 53-2 v BlackpoolBlackpool 2-3 Gillingham |
| 29 | Sat 15 Feb 2020 | 52-1 v Doncaster RoversGillingham 2-1 Doncaster Rovers |
| 30 | Tue 18 Feb 2020 | 5 1-0 v Southend UnitedSouthend United 0-1 Gillingham |
| 31 | Sat 22 Feb 2020 | 50-0 v Lincoln CityLincoln City 0-0 Gillingham |
| 32 | Sat 29 Feb 2020 | 51-2 v AFC WimbledonGillingham 1-2 AFC Wimbledon |
| 33 | Sat 7 Mar 2020 | 52-2 v SunderlandSunderland 2-2 Gillingham |
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