| 1 | Tue 13 Aug 2019 | 3-1 v Ipswich TownLuton Town 3-1 Ipswich Town | Carabao Cup First Round |
| 2 | Tue 27 Aug 2019 | 3-0 v Cardiff CityCardiff City 0-3 Luton Town | Carabao Cup Second Round |
| 3 | Sat 31 Aug 2019 | 2-1 v Huddersfield TownLuton Town 2-1 Huddersfield Town | Sky Bet Championship |
| 4 | Tue 24 Sep 2019 | 0-4 v Leicester CityLuton Town 0-4 Leicester City | Carabao Cup Third Round |
| 5 | Sat 28 Sep 2019 | 2-1 v Blackburn RoversBlackburn Rovers 1-2 Luton Town | Sky Bet Championship |
| 6 | Sat 9 Nov 2019 | 0-3 v ReadingReading 3-0 Luton Town | Sky Bet Championship |
| 7 | Thu 26 Dec 2019 | 3-3 v FulhamLuton Town 3-3 Fulham | Sky Bet Championship |
| 8 | Sat 1 Feb 2020 | 1-0 v Macclesfield TownMacclesfield Town 0-1 Northampton Town | Sky Bet League Two |
| 9 | Sat 8 Feb 2020 | 0-1 v Port ValeNorthampton Town 0-1 Port Vale | Sky Bet League Two |
| 10 | Tue 11 Feb 2020 | 0-1 v Swindon TownNorthampton Town 0-1 Swindon Town | Sky Bet League Two |
| 11 | Sat 15 Feb 2020 | 2-3 v WalsallWalsall 3-2 Northampton Town | Sky Bet League Two |
| 12 | Sat 22 Feb 2020 | 2-0 v Exeter CityNorthampton Town 2-0 Exeter City | Sky Bet League Two |
| 13 | Tue 25 Feb 2020 | 1-2 v Cheltenham TownCheltenham Town 2-1 Northampton Town | Sky Bet League Two |
| 14 | Sat 7 Mar 2020 | 1-2 v Mansfield TownNorthampton Town 1-2 Mansfield Town | Sky Bet League Two |
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