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