| 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 | Tue 20 Aug 2019 | 1-0 v Swindon TownSwindon Town 0-1 Northampton Town | Sky Bet League Two |
| 6 | Tue 3 Sep 2019 | 0-2 v Peterborough UnitedNorthampton Town 0-2 Peterborough United | Leasing.com Trophy Southern Group H |
| 7 | Sat 14 Sep 2019 | 2-0 v Newport CountyNorthampton Town 2-0 Newport County | Sky Bet League Two |
| 8 | Tue 17 Sep 2019 | 1-0 v StevenageStevenage 0-1 Northampton Town | 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 19 Oct 2019 | 2-0 v Salford CityNorthampton Town 2-0 Salford City | Sky Bet League Two |
| 15 | Tue 22 Oct 2019 | 2-0 v Carlisle UnitedCarlisle United 0-2 Northampton Town | Sky Bet League Two |
| 16 | Sat 26 Oct 2019 | 2-0 v Cambridge UnitedNorthampton Town 2-0 Cambridge United | Sky Bet League Two |
| 17 | Sat 2 Nov 2019 | 2-2 v Oldham AthleticOldham Athletic 2-2 Northampton Town | Sky Bet League Two |
| 18 | Sun 10 Nov 2019 | 3-0 v Chippenham TownChippenham Town 0-3 Northampton Town | Emirates FA Cup First Round |
| 19 | Sat 16 Nov 2019 | 4-1 v Crewe AlexandraNorthampton Town 4-1 Crewe Alexandra | Sky Bet League Two |
| 20 | Sat 23 Nov 2019 | 2-0 v Grimsby TownNorthampton Town 2-0 Grimsby Town | Sky Bet League Two |
| 21 | Sun 1 Dec 2019 | 3-1 v Notts CountyNorthampton Town 3-1 Notts County | Emirates FA Cup Second Round |
| 22 | Tue 3 Dec 2019 | 1-2 v PortsmouthPortsmouth 2-1 Northampton Town | Leasing.com Trophy Second Round |
| 23 | Sat 7 Dec 2019 | 2-3 v Exeter CityExeter City 3-2 Northampton Town | Sky Bet League Two |
| 24 | Sat 14 Dec 2019 | 1-0 v Forest Green RoversNorthampton Town 1-0 Forest Green Rovers | Sky Bet League Two |
| 25 | Sat 21 Dec 2019 | 1-1 v Mansfield TownMansfield Town 1-1 Northampton Town | Sky Bet League Two |
| 26 | Thu 26 Dec 2019 | 0-4 v Crawley TownCrawley Town 4-0 Northampton Town | Sky Bet League Two |
| 27 | Sun 29 Dec 2019 | 1-1 v Cheltenham TownNorthampton Town 1-1 Cheltenham Town | Sky Bet League Two |
| 28 | Wed 1 Jan 2020 | 1-0 v StevenageNorthampton Town 1-0 Stevenage | Sky Bet League Two |
| 29 | Sun 5 Jan 2020 | 4-2 v Burton AlbionBurton Albion 2-4 Northampton Town | Emirates FA Cup Third Round |
| 30 | Sat 11 Jan 2020 | 2-1 v Salford CitySalford City 1-2 Northampton Town | Sky Bet League Two |
| 31 | Sat 18 Jan 2020 | 4-1 v MorecambeNorthampton Town 4-1 Morecambe | Sky Bet League Two |
| 32 | Tue 21 Jan 2020 | 1-1 v Leyton OrientLeyton Orient 1-1 Northampton Town | Sky Bet League Two |
| 33 | Tue 4 Feb 2020 | 2-4 v Derby CountyDerby County 4-2 Northampton Town | Emirates FA Cup Fourth Round Replay |
| 34 | Sat 8 Feb 2020 | 0-1 v Port ValeNorthampton Town 0-1 Port Vale | Sky Bet League Two |
| 35 | Tue 11 Feb 2020 | 0-1 v Swindon TownNorthampton Town 0-1 Swindon Town | Sky Bet League Two |
| 36 | Sat 15 Feb 2020 | 2-3 v WalsallWalsall 3-2 Northampton Town | Sky Bet League Two |
| 37 | Tue 25 Feb 2020 | 1-2 v Cheltenham TownCheltenham Town 2-1 Northampton Town | Sky Bet League Two |
| 38 | Sat 29 Feb 2020 | 3-0 v Grimsby TownGrimsby Town 0-3 Northampton Town | Sky Bet League Two |
| 39 | Sat 7 Mar 2020 | 1-2 v Mansfield TownNorthampton Town 1-2 Mansfield Town | Sky Bet League Two |
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