| 1 | Tue 24 Jul 2018 | 12-1 v MillwallColchester United 2-1 Millwall | Friendly |
| 2 | Sat 4 Aug 2018 | 10-0 v Notts CountyNotts County 0-0 Colchester United | Sky Bet League Two |
| 3 | Sat 11 Aug 2018 | 12-0 v Port ValeColchester United 2-0 Port Vale | Sky Bet League Two |
| 4 | Tue 14 Aug 2018 | 12-2 v Cheltenham TownCheltenham Town 2-2 Colchester United | Carabao Cup First Round |
| 5 | Sat 18 Aug 2018 | 11-1 v Mansfield TownMansfield Town 1-1 Colchester United | Sky Bet League Two |
| 6 | Tue 21 Aug 2018 | 16-0 v Crewe AlexandraColchester United 6-0 Crewe Alexandra | Sky Bet League Two |
| 7 | Sat 25 Aug 2018 | 11-2 v Northampton TownColchester United 1-2 Northampton Town | Sky Bet League Two |
| 8 | Sat 1 Sep 2018 | 13-1 v Cheltenham TownCheltenham Town 1-3 Colchester United | Sky Bet League Two |
| 9 | Sat 8 Sep 2018 | 11-1 v Tranmere RoversTranmere Rovers 1-1 Colchester United | Sky Bet League Two |
| 10 | Sat 15 Sep 2018 | 13-0 v Cambridge UnitedColchester United 3-0 Cambridge United | Sky Bet League Two |
| 11 | Sat 22 Sep 2018 | 1 3-3 v Oldham AthleticOldham Athletic 3-3 Colchester United | Sky Bet League Two |
| 12 | Sat 29 Sep 2018 | 11-2 v BuryColchester United 1-2 Bury | Sky Bet League Two |
| 13 | Tue 2 Oct 2018 | 13-1 v Yeovil TownColchester United 3-1 Yeovil Town | Sky Bet League Two |
| 14 | Sat 6 Oct 2018 | 11-3 v StevenageStevenage 3-1 Colchester United | Sky Bet League Two |
| 15 | Sat 10 Nov 2018 | 10-1 v Accrington StanleyAccrington Stanley 1-0 Colchester United | Emirates FA Cup First Round |
| 16 | Tue 13 Nov 2018 | 11-3 v Cambridge UnitedCambridge United 3-1 Colchester United | Checkatrade Trophy Southern Group B |
| 17 | Sat 17 Nov 2018 | 10-2 v Newport CountyNewport County 2-0 Colchester United | Sky Bet League Two |
| 18 | Sat 24 Nov 2018 | 11-1 v Exeter CityColchester United 1-1 Exeter City | Sky Bet League Two |
| 19 | Tue 27 Nov 2018 | 11-0 v Forest Green RoversForest Green Rovers 0-1 Colchester United | Sky Bet League Two |
| 20 | Sat 8 Dec 2018 | 11-0 v Macclesfield TownColchester United 1-0 Macclesfield Town | Sky Bet League Two |
| 21 | Sat 15 Dec 2018 | 10-4 v Carlisle UnitedCarlisle United 4-0 Colchester United | Sky Bet League Two |
| 22 | Sat 23 Mar 2019 | 10-2 v Tranmere RoversColchester United 0-2 Tranmere Rovers | Sky Bet League Two |
| 23 | Sat 30 Mar 2019 | 11-0 v Cambridge UnitedCambridge United 0-1 Colchester United | Sky Bet League Two |
| 24 | Sat 6 Apr 2019 | 10-2 v Oldham AthleticColchester United 0-2 Oldham Athletic | Sky Bet League Two |
| 25 | Fri 19 Apr 2019 | 11-0 v Grimsby TownColchester United 1-0 Grimsby Town | Sky Bet League Two |
| 26 | Mon 22 Apr 2019 | 1 1-1 v Yeovil TownYeovil Town 1-1 Colchester United | Sky Bet League Two |
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