| 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 |
| 17 | Sat 20 Dec | 104-1 v Newport CountyColchester United 4-1 Newport County | Sky Bet League Two |
| 18 | Fri 26 Dec | 101-1 v Crawley TownCrawley Town 1-1 Colchester United | Sky Bet League Two |
| 19 | Mon 29 Dec | 101-1 v GillinghamGillingham 1-1 Colchester United | Sky Bet League Two |
| 20 | Thu 1 Jan | 10 1-0 v Milton Keynes DonsColchester United 1-0 Milton Keynes Dons | Sky Bet League Two |
| 21 | Sat 17 Jan | 101-0 v Bristol RoversBristol Rovers 0-1 Colchester United | Sky Bet League Two |
| 22 | Sat 24 Jan | 102-1 v Fleetwood TownColchester United 2-1 Fleetwood Town | Sky Bet League Two |
| 23 | Tue 27 Jan | 100-1 v Grimsby TownColchester United 0-1 Grimsby Town | Sky Bet League Two |
| 24 | Sat 31 Jan | 10 0-1 v Crewe AlexandraCrewe Alexandra 1-0 Colchester United | Sky Bet League Two |
| 25 | Sat 7 Feb | 102-0 v Shrewsbury TownColchester United 2-0 Shrewsbury Town | Sky Bet League Two |
| 26 | Sat 14 Feb | 100-1 v BarrowBarrow 1-0 Colchester United | Sky Bet League Two |
| 27 | Tue 17 Feb | 101-1 v Cambridge UnitedCambridge United 1-1 Colchester United | Sky Bet League Two |
| 28 | Sat 21 Feb | 104-1 v BarnetColchester United 4-1 Barnet | Sky Bet League Two |
| 29 | Sat 28 Feb | 100-1 v Salford CityColchester United 0-1 Salford City | Sky Bet League Two |
| 30 | Tue 3 Mar | 100-3 v ChesterfieldChesterfield 3-0 Colchester United | Sky Bet League Two |
| 31 | Sat 7 Mar | 102-1 v Newport CountyNewport County 1-2 Colchester United | Sky Bet League Two |
| 32 | Fri 13 Mar | 100-0 v Crawley TownColchester United 0-0 Crawley Town | Sky Bet League Two |
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