| 1 | Tue 13 Aug 2019 | 1-1 v BrentfordBrentford 1-1 Cambridge United | Carabao Cup First Round |
| 2 | Wed 28 Aug 2019 | 0-6 v Swansea CitySwansea City 6-0 Cambridge United | Carabao Cup Second Round |
| 3 | Tue 8 Oct 2019 | 0-1 v Northampton TownCambridge United 0-1 Northampton Town | Leasing.com Trophy Southern Group H |
| 4 | Sat 9 Nov 2019 | 1-1 v Exeter CityCambridge United 1-1 Exeter City | Emirates FA Cup First Round |
| 5 | Tue 12 Nov 2019 | 1-2 v Peterborough UnitedPeterborough United 2-1 Cambridge United | Leasing.com Trophy Southern Group H |
| 6 | Tue 19 Nov 2019 | 0-1 v Exeter CityExeter City 1-0 Cambridge United | Emirates FA Cup First Round Replay |
| 7 | Sun 29 Dec 2019 | 1-0 v MorecambeCambridge United 1-0 Morecambe | Sky Bet League Two |
| 8 | Wed 1 Jan 2020 | 2-3 v Mansfield TownCambridge United 2-3 Mansfield Town | Sky Bet League Two |
| 9 | Sat 4 Jan 2020 | 0-1 v Macclesfield TownMacclesfield Town 1-0 Cambridge United | Sky Bet League Two |
| 10 | Sat 1 Feb 2020 | 2-1 v Colchester UnitedCambridge United 2-1 Colchester United | Sky Bet League Two |
| 11 | Sat 8 Feb 2020 | 1-0 v Newport CountyNewport County 0-1 Cambridge United | Sky Bet League Two |
| 12 | Tue 11 Feb 2020 | 2-0 v Scunthorpe UnitedScunthorpe United 0-2 Cambridge United | Sky Bet League Two |
| 13 | Sat 15 Feb 2020 | 2-1 v Bradford CityCambridge United 2-1 Bradford City | Sky Bet League Two |
| 14 | Sat 22 Feb 2020 | 0-0 v Plymouth ArgylePlymouth Argyle 0-0 Cambridge United | Sky Bet League Two |
| 15 | Sat 29 Feb 2020 | 1-2 v Carlisle UnitedCambridge United 1-2 Carlisle United | Sky Bet League Two |
| 16 | Sat 7 Mar 2020 | 1-2 v Leyton OrientLeyton Orient 2-1 Cambridge United | Sky Bet League Two |
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