| 1 | Sat 3 Aug 2019 | 0-1 v WalsallNorthampton Town 0-1 Walsall | Sky Bet League Two |
| 2 | Sat 10 Aug 2019 | 1-1 v Port ValePort Vale 1-1 Northampton Town | Sky Bet League Two |
| 3 | Tue 13 Aug 2019 | 1-3 v Swansea CitySwansea City 3-1 Northampton Town | Carabao Cup First Round |
| 4 | Sat 17 Aug 2019 | 1-2 v Macclesfield TownNorthampton Town 1-2 Macclesfield Town | Sky Bet League Two |
| 5 | Sat 24 Aug 2019 | 0-1 v Colchester UnitedColchester United 1-0 Northampton Town | Sky Bet League Two |
| 6 | Sat 31 Aug 2019 | 3-1 v Plymouth ArgyleNorthampton Town 3-1 Plymouth Argyle | Sky Bet League Two |
| 7 | Tue 3 Sep 2019 | 0-2 v Peterborough UnitedNorthampton Town 0-2 Peterborough United | Leasing.com Trophy Southern Group H |
| 8 | Sat 14 Sep 2019 | 2-0 v Newport CountyNorthampton Town 2-0 Newport County | Sky Bet League Two |
| 9 | Sat 21 Sep 2019 | 2-2 v Crawley TownNorthampton Town 2-2 Crawley Town | Sky Bet League Two |
| 10 | Sat 28 Sep 2019 | 2-2 v MorecambeMorecambe 2-2 Northampton Town | Sky Bet League Two |
| 11 | Sat 5 Oct 2019 | 0-1 v Leyton OrientNorthampton Town 0-1 Leyton Orient | Sky Bet League Two |
| 12 | Tue 8 Oct 2019 | 1-0 v Cambridge UnitedCambridge United 0-1 Northampton Town | Leasing.com Trophy Southern Group H |
| 13 | Sat 12 Oct 2019 | 0-3 v Scunthorpe UnitedScunthorpe United 3-0 Northampton Town | Sky Bet League Two |
| 14 | Sat 2 Nov 2019 | 2-2 v Oldham AthleticOldham Athletic 2-2 Northampton Town | Sky Bet League Two |
| 15 | Sun 10 Nov 2019 | 3-0 v Chippenham TownChippenham Town 0-3 Northampton Town | Emirates FA Cup First Round |
| 16 | Sat 16 Nov 2019 | 4-1 v Crewe AlexandraNorthampton Town 4-1 Crewe Alexandra | Sky Bet League Two |
| 17 | Sun 1 Dec 2019 | 3-1 v Notts CountyNorthampton Town 3-1 Notts County | Emirates FA Cup Second Round |
| 18 | Tue 3 Dec 2019 | 1-2 v PortsmouthPortsmouth 2-1 Northampton Town | Leasing.com Trophy Second Round |
| 19 | Wed 1 Jan 2020 | 1-0 v StevenageNorthampton Town 1-0 Stevenage | Sky Bet League Two |
| 20 | Sun 5 Jan 2020 | 4-2 v Burton AlbionBurton Albion 2-4 Northampton Town | Emirates FA Cup Third Round |
| 21 | Sat 11 Jan 2020 | 2-1 v Salford CitySalford City 1-2 Northampton Town | Sky Bet League Two |
| 22 | Sat 18 Jan 2020 | 4-1 v MorecambeNorthampton Town 4-1 Morecambe | Sky Bet League Two |
| 23 | Tue 21 Jan 2020 | 1-1 v Leyton OrientLeyton Orient 1-1 Northampton Town | Sky Bet League Two |
| 24 | Tue 4 Feb 2020 | 2-4 v Derby CountyDerby County 4-2 Northampton Town | Emirates FA Cup Fourth Round Replay |
| 25 | Sat 8 Feb 2020 | 0-1 v Port ValeNorthampton Town 0-1 Port Vale | Sky Bet League Two |
| 26 | Sat 15 Feb 2020 | 2-3 v WalsallWalsall 3-2 Northampton Town | Sky Bet League Two |
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