| 1 | Sat 2 Aug | 51-1 v Tranmere RoversColchester United 1-1 Tranmere Rovers | Sky Bet League Two |
| 2 | Sat 9 Aug | 51-1 v Oldham AthleticOldham Athletic 1-1 Colchester United | Sky Bet League Two |
| 3 | Tue 12 Aug | 50-1 v Oxford UnitedOxford United 1-0 Colchester United | Carabao Cup First Round |
| 4 | Sat 16 Aug | 52-0 v Shrewsbury TownShrewsbury Town 0-2 Colchester United | Sky Bet League Two |
| 5 | Tue 19 Aug | 51-2 v Cambridge UnitedColchester United 1-2 Cambridge United | Sky Bet League Two |
| 6 | Sat 23 Aug | 50-2 v BarrowColchester United 0-2 Barrow | Sky Bet League Two |
| 7 | Sat 30 Aug | 51-1 v BarnetBarnet 1-1 Colchester United | Sky Bet League Two |
| 8 | Tue 2 Sep | 52-1 v Wycombe WanderersWycombe Wanderers 1-2 Colchester United | EFL Trophy Southern Group G |
| 9 | Sat 6 Sep | 5 1-1 v Crewe AlexandraColchester United 1-1 Crewe Alexandra | Sky Bet League Two |
| 10 | Sat 13 Sep | 50-1 v Accrington StanleyAccrington Stanley 1-0 Colchester United | Sky Bet League Two |
| 11 | Sat 20 Sep | 51-1 v Bristol RoversColchester United 1-1 Bristol Rovers | Sky Bet League Two |
| 12 | Sat 27 Sep | 52-4 v Fleetwood TownFleetwood Town 4-2 Colchester United | Sky Bet League Two |
| 13 | Sat 4 Oct | 56-2 v ChesterfieldColchester United 6-2 Chesterfield | Sky Bet League Two |
| 14 | Tue 7 Oct | 52-1 v GillinghamColchester United 2-1 Gillingham | EFL Trophy Southern Group G |
| 15 | Sat 11 Oct | 5 2-1 v Grimsby TownGrimsby Town 1-2 Colchester United | Sky Bet League Two |
| 16 | Sat 18 Oct | 53-1 v Harrogate TownColchester United 3-1 Harrogate Town | Sky Bet League Two |
| 17 | Sat 25 Oct | 50-0 v Swindon TownSwindon Town 0-0 Colchester United | Sky Bet League Two |
| 18 | Sat 1 Nov | 52-3 v Milton Keynes DonsColchester United 2-3 Milton Keynes Dons | Emirates FA Cup First Round |
| 19 | Sat 8 Nov | 50-2 v BromleyColchester United 0-2 Bromley | Sky Bet League Two |
| 20 | Sat 15 Nov | 52-0 v WalsallWalsall 0-2 Colchester United | Sky Bet League Two |
| 21 | Sat 22 Nov | 53-1 v Notts CountyNotts County 1-3 Colchester United | Sky Bet League Two |
| 22 | Sat 29 Nov | 52-0 v Cheltenham TownColchester United 2-0 Cheltenham Town | Sky Bet League Two |
| 23 | Sat 6 Dec | 50-0 v GillinghamColchester United 0-0 Gillingham | Sky Bet League Two |
| 24 | Sat 13 Dec | 53-4 v Salford CitySalford City 4-3 Colchester United | Sky Bet League Two |
| 25 | Sat 20 Dec | 54-1 v Newport CountyColchester United 4-1 Newport County | Sky Bet League Two |
| 26 | Fri 26 Dec | 51-1 v Crawley TownCrawley Town 1-1 Colchester United | Sky Bet League Two |
| 27 | Mon 29 Dec | 51-1 v GillinghamGillingham 1-1 Colchester United | Sky Bet League Two |
| 28 | Thu 1 Jan | 51-0 v Milton Keynes DonsColchester United 1-0 Milton Keynes Dons | Sky Bet League Two |
| 29 | Sat 17 Jan | 51-0 v Bristol RoversBristol Rovers 0-1 Colchester United | Sky Bet League Two |
| 30 | Sat 24 Jan | 52-1 v Fleetwood TownColchester United 2-1 Fleetwood Town | Sky Bet League Two |
| 31 | Tue 27 Jan | 50-1 v Grimsby TownColchester United 0-1 Grimsby Town | Sky Bet League Two |
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