| 1 | Sat 5 Sep 2020 | 11-3 v ReadingReading 3-1 Colchester United | Carabao Cup First Round South |
| 2 | Sat 19 Sep 2020 | 12-0 v Bolton WanderersColchester United 2-0 Bolton Wanderers | Sky Bet League Two |
| 3 | Sat 26 Sep 2020 | 11-1 v BarrowBarrow 1-1 Colchester United | Sky Bet League Two |
| 4 | Sat 3 Oct 2020 | 13-3 v Oldham AthleticColchester United 3-3 Oldham Athletic | Sky Bet League Two |
| 5 | Sat 10 Oct 2020 | 11-1 v WalsallWalsall 1-1 Colchester United | Sky Bet League Two |
| 6 | Sat 17 Oct 2020 | 12-3 v Carlisle UnitedCarlisle United 3-2 Colchester United | Sky Bet League Two |
| 7 | Tue 20 Oct 2020 | 11-0 v Forest Green RoversColchester United 1-0 Forest Green Rovers | Sky Bet League Two |
| 8 | Sat 24 Oct 2020 | 12-1 v Harrogate TownColchester United 2-1 Harrogate Town | Sky Bet League Two |
| 9 | Tue 27 Oct 2020 | 11-2 v Newport CountyNewport County 2-1 Colchester United | Sky Bet League Two |
| 10 | Tue 3 Nov 2020 | 13-1 v StevenageColchester United 3-1 Stevenage | Sky Bet League Two |
| 11 | Sat 14 Nov 2020 | 12-1 v Leyton OrientColchester United 2-1 Leyton Orient | Sky Bet League Two |
| 12 | Fri 20 Nov 2020 | 11-1 v Mansfield TownMansfield Town 1-1 Colchester United | Sky Bet League Two |
| 13 | Tue 24 Nov 2020 | 11-6 v Exeter CityExeter City 6-1 Colchester United | Sky Bet League Two |
| 14 | Tue 1 Dec 2020 | 11-1 v Crawley TownColchester United 1-1 Crawley Town | Sky Bet League Two |
| 15 | Sat 5 Dec 2020 | 12-1 v Grimsby TownColchester United 2-1 Grimsby Town | Sky Bet League Two |
| 16 | Tue 8 Dec 2020 | 11-0 v Scunthorpe UnitedScunthorpe United 0-1 Colchester United | Sky Bet League Two |
| 17 | Sat 12 Dec 2020 | 11-1 v Port ValePort Vale 1-1 Colchester United | Sky Bet League Two |
| 18 | Tue 15 Dec 2020 | 11-2 v Cambridge UnitedCambridge United 2-1 Colchester United | Sky Bet League Two |
| 19 | Sat 19 Dec 2020 | 11-2 v MorecambeColchester United 1-2 Morecambe | Sky Bet League Two |
| 20 | Sat 26 Dec 2020 | 10-2 v Southend UnitedSouthend United 2-0 Colchester United | Sky Bet League Two |
| 21 | Tue 29 Dec 2020 | 10-0 v Cheltenham TownColchester United 0-0 Cheltenham Town | Sky Bet League Two |
| 22 | Sat 16 Jan 2021 | 11-1 v Cambridge UnitedColchester United 1-1 Cambridge United | Sky Bet League Two |
| 23 | Sat 23 Jan 2021 | 10-3 v MorecambeMorecambe 3-0 Colchester United | Sky Bet League Two |
| 24 | Tue 26 Jan 2021 | 10-0 v StevenageStevenage 0-0 Colchester United | Sky Bet League Two |
| 25 | Fri 29 Jan 2021 | 10-1 v Scunthorpe UnitedColchester United 0-1 Scunthorpe United | Sky Bet League Two |
| 26 | Sat 20 Feb 2021 | 10-1 v Crawley TownCrawley Town 1-0 Colchester United | Sky Bet League Two |
| 27 | Tue 23 Feb 2021 | 11-2 v Exeter CityColchester United 1-2 Exeter City | Sky Bet League Two |
| 28 | Sat 27 Feb 2021 | 10-3 v Forest Green RoversForest Green Rovers 3-0 Colchester United | Sky Bet League Two |
| 29 | Tue 23 Mar 2021 | 12-2 v Tranmere RoversColchester United 2-2 Tranmere Rovers | Sky Bet League Two |
| 30 | Sat 27 Mar 2021 | 11-2 v Bradford CityColchester United 1-2 Bradford City | Sky Bet League Two |
| 31 | Fri 2 Apr 2021 | 10-0 v Bolton WanderersBolton Wanderers 0-0 Colchester United | Sky Bet League Two |
| 32 | Mon 5 Apr 2021 | 11-1 v BarrowColchester United 1-1 Barrow | Sky Bet League Two |
| 33 | Fri 9 Apr 2021 | 12-5 v Oldham AthleticOldham Athletic 5-2 Colchester United | Sky Bet League Two |
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