| 1 | Sat 10 Aug 2019 | 40-1 v Plymouth ArgylePlymouth Argyle 1-0 Colchester United | Sky Bet League Two |
| 2 | Tue 13 Aug 2019 | 43-0 v Swindon TownColchester United 3-0 Swindon Town | Carabao Cup First Round |
| 3 | Sat 7 Sep 2019 | 40-0 v WalsallColchester United 0-0 Walsall | Sky Bet League Two |
| 4 | Sat 14 Sep 2019 | 4 0-1 v Forest Green RoversForest Green Rovers 1-0 Colchester United | Sky Bet League Two |
| 5 | Tue 24 Sep 2019 | 40-0 v Tottenham HotspurColchester United 0-0 Tottenham Hotspur | Carabao Cup Third Round |
| 6 | Sat 28 Sep 2019 | 41-1 v Macclesfield TownMacclesfield Town 1-1 Colchester United | Sky Bet League Two |
| 7 | Sat 12 Oct 2019 | 41-2 v Crawley TownCrawley Town 2-1 Colchester United | Sky Bet League Two |
| 8 | Sat 19 Oct 2019 | 40-1 v MorecambeColchester United 0-1 Morecambe | Sky Bet League Two |
| 9 | Tue 29 Oct 2019 | 43-1 v Crawley TownCrawley Town 1-3 Colchester United | Carabao Cup Fourth Round |
| 10 | Sat 2 Nov 2019 | 43-2 v Mansfield TownMansfield Town 2-3 Colchester United | Sky Bet League Two |
| 11 | Tue 12 Nov 2019 | 41-0 v Ipswich TownColchester United 1-0 Ipswich Town | Leasing.com Trophy Southern Group A |
| 12 | Sat 23 Nov 2019 | 41-1 v Cheltenham TownCheltenham Town 1-1 Colchester United | Sky Bet League Two |
| 13 | Sat 7 Dec 2019 | 41-0 v Salford CityColchester United 1-0 Salford City | Sky Bet League Two |
| 14 | Wed 18 Dec 2019 | 40-3 v Manchester UnitedManchester United 3-0 Colchester United | Carabao Cup Quarter Final |
| 15 | Sat 21 Dec 2019 | 43-0 v Carlisle UnitedColchester United 3-0 Carlisle United | Sky Bet League Two |
| 16 | Thu 26 Dec 2019 | 43-1 v Leyton OrientLeyton Orient 1-3 Colchester United | Sky Bet League Two |
| 17 | Sun 29 Dec 2019 | 4 2-2 v Exeter CityColchester United 2-2 Exeter City | Sky Bet League Two |
| 18 | Sat 4 Jan 2020 | 40-0 v StevenageStevenage 0-0 Colchester United | Sky Bet League Two |
| 19 | Sat 11 Jan 2020 | 41-1 v MorecambeMorecambe 1-1 Colchester United | Sky Bet League Two |
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