| 1 | Wed 9 Aug | 12-2 v Cardiff CityCardiff City 2-2 Colchester United | Carabao Cup First Round South |
| 2 | Tue 15 Aug | 10-2 v AFC WimbledonColchester United 0-2 AFC Wimbledon | Sky Bet League Two |
| 3 | Sat 19 Aug | 12-3 v Milton Keynes DonsColchester United 2-3 Milton Keynes Dons | Sky Bet League Two |
| 4 | Sat 26 Aug | 13-0 v GillinghamGillingham 0-3 Colchester United | Sky Bet League Two |
| 5 | Sat 2 Sep | 10-1 v WalsallWalsall 1-0 Colchester United | Sky Bet League Two |
| 6 | Sat 9 Sep | 12-0 v Tranmere RoversColchester United 2-0 Tranmere Rovers | Sky Bet League Two |
| 7 | Sat 16 Sep | 11-1 v Mansfield TownColchester United 1-1 Mansfield Town | Sky Bet League Two |
| 8 | Sat 23 Sep | 11-2 v Crewe AlexandraCrewe Alexandra 2-1 Colchester United | Sky Bet League Two |
| 9 | Sat 30 Sep | 1 5-4 v Notts CountyColchester United 5-4 Notts County | Sky Bet League Two |
| 10 | Tue 3 Oct | 11-2 v Newport CountyNewport County 2-1 Colchester United | Sky Bet League Two |
| 11 | Sat 7 Oct | 11-3 v MorecambeColchester United 1-3 Morecambe | Sky Bet League Two |
| 12 | Sat 21 Oct | 11-2 v Harrogate TownColchester United 1-2 Harrogate Town | Sky Bet League Two |
| 13 | Tue 24 Oct | 13-2 v Grimsby TownGrimsby Town 2-3 Colchester United | Sky Bet League Two |
| 14 | Sat 28 Oct | 11-0 v Accrington StanleyAccrington Stanley 0-1 Colchester United | Sky Bet League Two |
| 15 | Sat 4 Nov | 12-3 v Shrewsbury TownShrewsbury Town 3-2 Colchester United | Emirates FA Cup First Round |
| 16 | Tue 7 Nov | 13-1 v Swindon TownColchester United 3-1 Swindon Town | Sky Bet League Two |
| 17 | Sat 11 Nov | 11-1 v Sutton UnitedColchester United 1-1 Sutton United | Sky Bet League Two |
| 18 | Sat 18 Nov | 10-2 v Stockport CountyStockport County 2-0 Colchester United | Sky Bet League Two |
| 19 | Sat 9 Dec | 11-2 v Crawley TownColchester United 1-2 Crawley Town | Sky Bet League Two |
| 20 | Sat 16 Dec | 11-2 v WrexhamWrexham 2-1 Colchester United | Sky Bet League Two |
| 21 | Fri 22 Dec | 12-1 v Salford CityColchester United 2-1 Salford City | Sky Bet League Two |
| 22 | Tue 26 Dec | 10-1 v Milton Keynes DonsMilton Keynes Dons 1-0 Colchester United | Sky Bet League Two |
| 23 | Fri 29 Dec | 13-5 v AFC WimbledonAFC Wimbledon 5-3 Colchester United | Sky Bet League Two |
| 24 | Mon 1 Jan | 10-1 v GillinghamColchester United 0-1 Gillingham | Sky Bet League Two |
| 25 | Sat 6 Jan | 12-2 v Swindon TownSwindon Town 2-2 Colchester United | Sky Bet League Two |
| 26 | Sat 13 Jan | 11-1 v Bradford CityColchester United 1-1 Bradford City | Sky Bet League Two |
| 27 | Sat 27 Jan | 11-0 v MorecambeMorecambe 0-1 Colchester United | Sky Bet League Two |
| 28 | Sat 3 Feb | 13-3 v Forest Green RoversColchester United 3-3 Forest Green Rovers | Sky Bet League Two |
| 29 | Sat 10 Feb | 1 0-1 v Harrogate TownHarrogate Town 1-0 Colchester United | Sky Bet League Two |
| 30 | Sat 17 Feb | 11-1 v Accrington StanleyColchester United 1-1 Accrington Stanley | Sky Bet League Two |
| 31 | Sat 24 Feb | 11-1 v Sutton UnitedSutton United 1-1 Colchester United | Sky Bet League Two |
| 32 | Tue 27 Feb | 11-1 v Salford CitySalford City 1-1 Colchester United | Sky Bet League Two |
| 33 | Sat 9 Mar | 10-2 v BarrowBarrow 2-0 Colchester United | Sky Bet League Two |
| 34 | Sat 16 Mar | 11-1 v WalsallColchester United 1-1 Walsall | Sky Bet League Two |
| 35 | Sat 23 Mar | 11-1 v Mansfield TownMansfield Town 1-1 Colchester United | Sky Bet League Two |
| 36 | Fri 29 Mar | 12-1 v Newport CountyColchester United 2-1 Newport County | Sky Bet League Two |
| 37 | Mon 1 Apr | 11-1 v Tranmere RoversTranmere Rovers 1-1 Colchester United | Sky Bet League Two |
| 38 | Sat 6 Apr | 11-2 v WrexhamColchester United 1-2 Wrexham | Sky Bet League Two |
| 39 | Tue 9 Apr | 11-2 v Stockport CountyColchester United 1-2 Stockport County | Sky Bet League Two |
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