| 1 | Sat 10 Aug 2019 | 0-0 v Newport CountyCambridge United 0-0 Newport County | Sky Bet League Two |
| 2 | Sat 17 Aug 2019 | 2-1 v Colchester UnitedColchester United 1-2 Cambridge United | Sky Bet League Two |
| 3 | Sat 24 Aug 2019 | 1-2 v Oldham AthleticCambridge United 1-2 Oldham Athletic | Sky Bet League Two |
| 4 | Wed 28 Aug 2019 | 0-6 v Swansea CitySwansea City 6-0 Cambridge United | Carabao Cup Second Round |
| 5 | Sat 31 Aug 2019 | 0-1 v Port ValePort Vale 1-0 Cambridge United | Sky Bet League Two |
| 6 | Sat 7 Sep 2019 | 0-1 v Forest Green RoversCambridge United 0-1 Forest Green Rovers | Sky Bet League Two |
| 7 | Sat 14 Sep 2019 | 3-2 v Crewe AlexandraCrewe Alexandra 2-3 Cambridge United | Sky Bet League Two |
| 8 | Tue 17 Sep 2019 | 4-0 v Mansfield TownMansfield Town 0-4 Cambridge United | Sky Bet League Two |
| 9 | Sat 21 Sep 2019 | 0-1 v Swindon TownCambridge United 0-1 Swindon Town | Sky Bet League Two |
| 10 | Sat 28 Sep 2019 | 1-1 v StevenageStevenage 1-1 Cambridge United | Sky Bet League Two |
| 11 | Sat 5 Oct 2019 | 2-2 v Macclesfield TownCambridge United 2-2 Macclesfield Town | Sky Bet League Two |
| 12 | Tue 8 Oct 2019 | 0-1 v Northampton TownCambridge United 0-1 Northampton Town | Leasing.com Trophy Southern Group H |
| 13 | Sat 12 Oct 2019 | 0-1 v Salford CitySalford City 1-0 Cambridge United | Sky Bet League Two |
| 14 | Sat 19 Oct 2019 | 4-0 v Exeter CityCambridge United 4-0 Exeter City | Sky Bet League Two |
| 15 | Tue 22 Oct 2019 | 0-0 v Grimsby TownCambridge United 0-0 Grimsby Town | Sky Bet League Two |
| 16 | Sat 26 Oct 2019 | 0-2 v Northampton TownNorthampton Town 2-0 Cambridge United | Sky Bet League Two |
| 17 | Sat 2 Nov 2019 | 2-1 v Crawley TownCambridge United 2-1 Crawley Town | Sky Bet League Two |
| 18 | Sat 9 Nov 2019 | 1-1 v Exeter CityCambridge United 1-1 Exeter City | Emirates FA Cup First Round |
| 19 | Sat 16 Nov 2019 | 1-2 v WalsallWalsall 2-1 Cambridge United | Sky Bet League Two |
| 20 | Tue 19 Nov 2019 | 0-1 v Exeter CityExeter City 1-0 Cambridge United | Emirates FA Cup First Round Replay |
| 21 | Sat 23 Nov 2019 | 0-0 v Carlisle UnitedCarlisle United 0-0 Cambridge United | Sky Bet League Two |
| 22 | Sat 7 Dec 2019 | 1-0 v Plymouth ArgyleCambridge United 1-0 Plymouth Argyle | Sky Bet League Two |
| 23 | Sat 14 Dec 2019 | 1-1 v Cheltenham TownCheltenham Town 1-1 Cambridge United | Sky Bet League Two |
| 24 | Sat 21 Dec 2019 | 2-3 v Leyton OrientCambridge United 2-3 Leyton Orient | Sky Bet League Two |
| 25 | Thu 26 Dec 2019 | 0-4 v Swindon TownSwindon Town 4-0 Cambridge United | Sky Bet League Two |
| 26 | Sun 29 Dec 2019 | 1-0 v MorecambeCambridge United 1-0 Morecambe | Sky Bet League Two |
| 27 | Wed 1 Jan 2020 | 2-3 v Mansfield TownCambridge United 2-3 Mansfield Town | Sky Bet League Two |
| 28 | Sat 4 Jan 2020 | 0-1 v Macclesfield TownMacclesfield Town 1-0 Cambridge United | Sky Bet League Two |
| 29 | Sat 11 Jan 2020 | 0-2 v Exeter CityExeter City 2-0 Cambridge United | Sky Bet League Two |
| 30 | Sat 7 Mar 2020 | 1-2 v Leyton OrientLeyton Orient 2-1 Cambridge United | Sky Bet League Two |
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