| 1 | Tue 13 Aug 2019 | 332-2 v Newport CountyGillingham 2-2 Newport County | Carabao Cup First Round |
| 2 | Tue 20 Aug 2019 | 332-2 v BlackpoolGillingham 2-2 Blackpool | Sky Bet League One |
| 3 | Sat 24 Aug 2019 | 33 0-1 v Coventry CityCoventry City 1-0 Gillingham | Sky Bet League One |
| 4 | Sat 31 Aug 2019 | 335-0 v Bolton WanderersGillingham 5-0 Bolton Wanderers | Sky Bet League One |
| 5 | Sat 14 Sep 2019 | 332-0 v Wycombe WanderersGillingham 2-0 Wycombe Wanderers | Sky Bet League One |
| 6 | Tue 17 Sep 2019 | 331-1 v Bristol RoversBristol Rovers 1-1 Gillingham | Sky Bet League One |
| 7 | Sat 21 Sep 2019 | 33 0-1 v Ipswich TownGillingham 0-1 Ipswich Town | Sky Bet League One |
| 8 | Sat 28 Sep 2019 | 33 0-3 v Oxford UnitedOxford United 3-0 Gillingham | Sky Bet League One |
| 9 | Sat 5 Oct 2019 | 333-1 v Southend UnitedGillingham 3-1 Southend United | Sky Bet League One |
| 10 | Sat 12 Oct 2019 | 33 0-0 v PortsmouthPortsmouth 0-0 Gillingham | Sky Bet League One |
| 11 | Sat 19 Oct 2019 | 33 1-2 v Peterborough UnitedGillingham 1-2 Peterborough United | Sky Bet League One |
| 12 | Sat 26 Oct 2019 | 331-0 v Accrington StanleyAccrington Stanley 0-1 Gillingham | Sky Bet League One |
| 13 | Sat 2 Nov 2019 | 330-3 v Rotherham UnitedGillingham 0-3 Rotherham United | Sky Bet League One |
| 14 | Sat 9 Nov 2019 | 331-1 v SunderlandSunderland 1-1 Gillingham | Emirates FA Cup First Round |
| 15 | Sat 16 Nov 2019 | 33 1-0 v Lincoln CityGillingham 1-0 Lincoln City | Sky Bet League One |
| 16 | Tue 19 Nov 2019 | 331-0 v SunderlandGillingham 1-0 Sunderland | Emirates FA Cup First Round Replay |
| 17 | Sat 23 Nov 2019 | 33 0-1 v AFC WimbledonAFC Wimbledon 1-0 Gillingham | Sky Bet League One |
| 18 | Sun 1 Dec 2019 | 333-0 v Doncaster RoversGillingham 3-0 Doncaster Rovers | Emirates FA Cup Second Round |
| 19 | Sat 7 Dec 2019 | 331-0 v SunderlandGillingham 1-0 Sunderland | Sky Bet League One |
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