| 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 | Tue 24 Sep 2019 | 0-0 v Tottenham HotspurColchester United 0-0 Tottenham Hotspur | Carabao Cup Third Round |
| 10 | Sat 5 Oct 2019 | 3-1 v StevenageColchester United 3-1 Stevenage | Sky Bet League Two |
| 11 | Sat 12 Oct 2019 | 1-2 v Crawley TownCrawley Town 2-1 Colchester United | Sky Bet League Two |
| 12 | Tue 12 Nov 2019 | 1-0 v Ipswich TownColchester United 1-0 Ipswich Town | Leasing.com Trophy Southern Group A |
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