| 1 | Sat 9 Aug | 101-1 v Oldham AthleticOldham Athletic 1-1 Colchester United | Sky Bet League Two |
| 2 | Tue 12 Aug | 100-1 v Oxford UnitedOxford United 1-0 Colchester United | Carabao Cup First Round |
| 3 | Sat 16 Aug | 10 2-0 v Shrewsbury TownShrewsbury Town 0-2 Colchester United | Sky Bet League Two |
| 4 | Tue 19 Aug | 10 1-2 v Cambridge UnitedColchester United 1-2 Cambridge United | Sky Bet League Two |
| 5 | Sat 23 Aug | 10 0-2 v BarrowColchester United 0-2 Barrow | Sky Bet League Two |
| 6 | Sat 30 Aug | 101-1 v BarnetBarnet 1-1 Colchester United | Sky Bet League Two |
| 7 | Tue 2 Sep | 102-1 v Wycombe WanderersWycombe Wanderers 1-2 Colchester United | EFL Trophy Southern Group G |
| 8 | Sat 6 Sep | 101-1 v Crewe AlexandraColchester United 1-1 Crewe Alexandra | Sky Bet League Two |
| 9 | Sat 13 Sep | 100-1 v Accrington StanleyAccrington Stanley 1-0 Colchester United | Sky Bet League Two |
| 10 | Sat 20 Sep | 101-1 v Bristol RoversColchester United 1-1 Bristol Rovers | Sky Bet League Two |
| 11 | Sat 27 Sep | 102-4 v Fleetwood TownFleetwood Town 4-2 Colchester United | Sky Bet League Two |
| 12 | Sat 4 Oct | 106-2 v ChesterfieldColchester United 6-2 Chesterfield | Sky Bet League Two |
| 13 | Tue 7 Oct | 102-1 v GillinghamColchester United 2-1 Gillingham | EFL Trophy Southern Group G |
| 14 | Sat 11 Oct | 10 2-1 v Grimsby TownGrimsby Town 1-2 Colchester United | Sky Bet League Two |
| 15 | Sat 18 Oct | 103-1 v Harrogate TownColchester United 3-1 Harrogate Town | Sky Bet League Two |
| 16 | Sat 25 Oct | 100-0 v Swindon TownSwindon Town 0-0 Colchester United | Sky Bet League Two |
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