| 1 | Sat 10 Aug 2019 | 0-1 v Plymouth ArgylePlymouth Argyle 1-0 Colchester United | Sky Bet League Two |
| 2 | Tue 13 Aug 2019 | 3-0 v Swindon TownColchester United 3-0 Swindon Town | Carabao Cup First Round |
| 3 | Sat 17 Aug 2019 | 1-2 v Cambridge UnitedColchester United 1-2 Cambridge United | Sky Bet League Two |
| 4 | Tue 20 Aug 2019 | 2-2 v Grimsby TownGrimsby Town 2-2 Colchester United | Sky Bet League Two |
| 5 | Sat 24 Aug 2019 | 1-0 v Northampton TownColchester United 1-0 Northampton Town | Sky Bet League Two |
| 6 | Tue 27 Aug 2019 | 0-0 v Crystal PalaceCrystal Palace 0-0 Colchester United | Carabao Cup Second Round |
| 7 | Sat 31 Aug 2019 | 1-0 v Oldham AthleticOldham Athletic 0-1 Colchester United | Sky Bet League Two |
| 8 | Sat 7 Sep 2019 | 0-0 v WalsallColchester United 0-0 Walsall | Sky Bet League Two |
| 9 | Sat 14 Sep 2019 | 0-1 v Forest Green RoversForest Green Rovers 1-0 Colchester United | Sky Bet League Two |
| 10 | Tue 17 Sep 2019 | 3-0 v Swindon TownSwindon Town 0-3 Colchester United | Sky Bet League Two |
| 11 | Sat 21 Sep 2019 | 2-1 v Leyton OrientColchester United 2-1 Leyton Orient | Sky Bet League Two |
| 12 | Tue 24 Sep 2019 | 0-0 v Tottenham HotspurColchester United 0-0 Tottenham Hotspur | Carabao Cup Third Round |
| 13 | Sat 28 Sep 2019 | 1-1 v Macclesfield TownMacclesfield Town 1-1 Colchester United | Sky Bet League Two |
| 14 | Sat 5 Oct 2019 | 3-1 v StevenageColchester United 3-1 Stevenage | Sky Bet League Two |
| 15 | Sat 12 Oct 2019 | 1-2 v Crawley TownCrawley Town 2-1 Colchester United | Sky Bet League Two |
| 16 | Sat 19 Oct 2019 | 0-1 v MorecambeColchester United 0-1 Morecambe | Sky Bet League Two |
| 17 | Tue 22 Oct 2019 | 0-0 v Crewe AlexandraCrewe Alexandra 0-0 Colchester United | Sky Bet League Two |
| 18 | Sat 26 Oct 2019 | 3-1 v Newport CountyColchester United 3-1 Newport County | Sky Bet League Two |
| 19 | Tue 29 Oct 2019 | 3-1 v Crawley TownCrawley Town 1-3 Colchester United | Carabao Cup Fourth Round |
| 20 | Sat 2 Nov 2019 | 3-2 v Mansfield TownMansfield Town 2-3 Colchester United | Sky Bet League Two |
| 21 | Sat 23 Nov 2019 | 1-1 v Cheltenham TownCheltenham Town 1-1 Colchester United | Sky Bet League Two |
| 22 | Sat 7 Dec 2019 | 1-0 v Salford CityColchester United 1-0 Salford City | Sky Bet League Two |
| 23 | Sat 14 Dec 2019 | 2-2 v Scunthorpe UnitedScunthorpe United 2-2 Colchester United | Sky Bet League Two |
| 24 | Wed 18 Dec 2019 | 0-3 v Manchester UnitedManchester United 3-0 Colchester United | Carabao Cup Quarter Final |
| 25 | Thu 26 Dec 2019 | 3-1 v Leyton OrientLeyton Orient 1-3 Colchester United | Sky Bet League Two |
| 26 | Sun 29 Dec 2019 | 2-2 v Exeter CityColchester United 2-2 Exeter City | Sky Bet League Two |
| 27 | Wed 1 Jan 2020 | 1-1 v Crawley TownColchester United 1-1 Crawley Town | Sky Bet League Two |
| 28 | Sat 4 Jan 2020 | 0-0 v StevenageStevenage 0-0 Colchester United | Sky Bet League Two |
| 29 | Sat 11 Jan 2020 | 1-1 v MorecambeMorecambe 1-1 Colchester United | Sky Bet League Two |
| 30 | Tue 21 Jan 2020 | 0-0 v Bradford CityColchester United 0-0 Bradford City | Sky Bet League Two |
| 31 | Sat 25 Jan 2020 | 0-0 v Exeter CityExeter City 0-0 Colchester United | Sky Bet League Two |
| 32 | Tue 28 Jan 2020 | 3-1 v Swindon TownColchester United 3-1 Swindon Town | Sky Bet League Two |
| 33 | Sat 1 Feb 2020 | 1-2 v Cambridge UnitedCambridge United 2-1 Colchester United | Sky Bet League Two |
| 34 | Sat 8 Feb 2020 | 3-0 v Plymouth ArgyleColchester United 3-0 Plymouth Argyle | Sky Bet League Two |
| 35 | Tue 11 Feb 2020 | 2-3 v Grimsby TownColchester United 2-3 Grimsby Town | Sky Bet League Two |
| 36 | Sat 15 Feb 2020 | 0-3 v Port ValePort Vale 3-0 Colchester United | Sky Bet League Two |
| 37 | Sat 22 Feb 2020 | 2-1 v Salford CitySalford City 1-2 Colchester United | Sky Bet League Two |
| 38 | Sat 29 Feb 2020 | 0-2 v Cheltenham TownColchester United 0-2 Cheltenham Town | Sky Bet League Two |
| 39 | Sat 7 Mar 2020 | 3-0 v Carlisle UnitedCarlisle United 0-3 Colchester United | Sky Bet League Two |
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