| 1 | 13/8/2019 | 1-3 v Swansea CitySwansea City 3-1 Northampton Town | Carabao Cup First Round |
| 2 | 17/8/2019 | 1-2 v Macclesfield TownNorthampton Town 1-2 Macclesfield Town | Sky Bet League Two |
| 3 | 20/8/2019 | 1-0 v Swindon TownSwindon Town 0-1 Northampton Town | Sky Bet League Two |
| 4 | 24/8/2019 | 0-1 v Colchester UnitedColchester United 1-0 Northampton Town | Sky Bet League Two |
| 5 | 31/8/2019 | 3-1 v Plymouth ArgyleNorthampton Town 3-1 Plymouth Argyle | Sky Bet League Two |
| 6 | 3/9/2019 | 0-2 v Peterborough UnitedNorthampton Town 0-2 Peterborough United | Checkatrade Trophy Southern Group H |
| 7 | 14/9/2019 | 2-0 v Newport CountyNorthampton Town 2-0 Newport County | Sky Bet League Two |
| 8 | 17/9/2019 | 1-0 v StevenageStevenage 0-1 Northampton Town | Sky Bet League Two |
| 9 | 21/9/2019 | 2-2 v Crawley TownNorthampton Town 2-2 Crawley Town | Sky Bet League Two |
| 10 | 5/10/2019 | 0-1 v Leyton OrientNorthampton Town 0-1 Leyton Orient | Sky Bet League Two |
| 11 | 8/10/2019 | 1-0 v Cambridge UnitedCambridge United 0-1 Northampton Town | Checkatrade Trophy Southern Group H |
| 12 | 12/10/2019 | 0-3 v Scunthorpe UnitedScunthorpe United 3-0 Northampton Town | Sky Bet League Two |
| 13 | 19/10/2019 | 2-0 v Salford CityNorthampton Town 2-0 Salford City | Sky Bet League Two |
| 14 | 22/10/2019 | 2-0 v Carlisle UnitedCarlisle United 0-2 Northampton Town | Sky Bet League Two |
| 15 | 26/10/2019 | 2-0 v Cambridge UnitedNorthampton Town 2-0 Cambridge United | Sky Bet League Two |
| 16 | 2/11/2019 | 2-2 v Oldham AthleticOldham Athletic 2-2 Northampton Town | Sky Bet League Two |
| 17 | 10/11/2019 | 3-0 v Chippenham TownChippenham Town 0-3 Northampton Town | Emirates FA Cup First Round |
| 18 | 16/11/2019 | 4-1 v Crewe AlexandraNorthampton Town 4-1 Crewe Alexandra | Sky Bet League Two |
| 19 | 3/12/2019 | 1-2 v PortsmouthPortsmouth 2-1 Northampton Town | Checkatrade Trophy Second Round |
