| 1 | 10/8/2019 | 0-1 v Plymouth ArgylePlymouth Argyle 1-0 Colchester United | Sky Bet League Two |
| 2 | 13/8/2019 | 3-0 v Swindon TownColchester United 3-0 Swindon Town | Carabao Cup First Round |
| 3 | 17/8/2019 | 1-2 v Cambridge UnitedColchester United 1-2 Cambridge United | Sky Bet League Two |
| 4 | 20/8/2019 | 2-2 v Grimsby TownGrimsby Town 2-2 Colchester United | Sky Bet League Two |
| 5 | 24/8/2019 | 1-0 v Northampton TownColchester United 1-0 Northampton Town | Sky Bet League Two |
| 6 | 27/8/2019 | 0-0 v Crystal PalaceCrystal Palace 0-0 Colchester United | Carabao Cup Second Round |
| 7 | 31/8/2019 | 1-0 v Oldham AthleticOldham Athletic 0-1 Colchester United | Sky Bet League Two |
| 8 | 7/9/2019 | 0-0 v WalsallColchester United 0-0 Walsall | Sky Bet League Two |
| 9 | 14/9/2019 | 0-1 v Forest Green RoversForest Green Rovers 1-0 Colchester United | Sky Bet League Two |
| 10 | 17/9/2019 | 3-0 v Swindon TownSwindon Town 0-3 Colchester United | Sky Bet League Two |
| 11 | 24/9/2019 | 0-0 v Tottenham HotspurColchester United 0-0 Tottenham Hotspur | Carabao Cup Third Round |
| 12 | 28/9/2019 | 1-1 v Macclesfield TownMacclesfield Town 1-1 Colchester United | Sky Bet League Two |
| 13 | 5/10/2019 | 3-1 v StevenageColchester United 3-1 Stevenage | Sky Bet League Two |
| 14 | 12/10/2019 | 1-2 v Crawley TownCrawley Town 2-1 Colchester United | Sky Bet League Two |
