Football League Cup 2023/24, First Round |
| 09.08.2023 | | Cardiff City | | Colchester United | | 2:2 (2:2), pen. 3:0 |
| Cardiff |
Football League Cup 2019/20, Third round |
| 24.09.2019 | | Colchester United | | Tottenham Hotspur | | 0:0, pen. 4:3 |
| Colchester |
Football League Cup 2019/20, Second round |
| 27.08.2019 | | Crystal Palace | | Colchester United | | 0:0, pen. 4:5 |
| London |
Football League Cup 2018/19, First Round |
| 14.08.2018 | | Cheltenham Town | | Colchester United | | 2:2 (1:0), pen. 6:5 |
| Cheltenham |
Football League Cup 2011/12, First Round |
| 09.08.2011 | | Wycombe Wanderers | | Colchester United | | 3:3 aet (2:2, 2:2), pen. 5:4 |
| High Wycombe |
Football League Cup 1999/00, First Round |
| 10.08.1999 | | Colchester United | | Crystal Palace | | 2:2 (1:0) |
| Colchester |
Football League Cup 1997/98, First Round |
| 26.08.1997 | | Luton Town | | Colchester United | | 1:1 (1:0) |
| Luton |
Football League Cup 1996/97, Second round |
| 17.09.1996 | | Huddersfield Town | | Colchester United | | 1:1 (1:0) |
| Huddersfield |
Football League Cup 1992/93, First Round |
| 18.08.1992 | | Colchester United | | Brighton & Hove Albion | | 1:1 (0:0) |
| Colchester |
Football League Cup 1988/89, First Round |
| 30.08.1988 | | Colchester United | | Northampton Town | | 0:0 |
| Colchester |
Football League Cup 1986/87, First Round |
| 26.08.1986 | | Colchester United | | Peterborough United | | 0:0 |
| Colchester |
Football League Cup 1983/84, Second round |
| 04.10.1983 | | Swansea City | | Colchester United | | 1:1 |
| |
Football League Cup 1982/83, Second round |
| 06.10.1982 | | Colchester United | | Southampton | | 0:0 |
| |
Football League Cup 1981/82, First Round |
| 15.09.1981 | | Gillingham | | Colchester United | | 1:1 |
| |
Football League Cup 1978/79, First Round |
| 15.08.1978 | | Charlton Athletic | | Colchester United | | 0:0 |
| |
Football League Cup 1977/78, Second round |
| 31.08.1977 | | Blackburn Rovers | | Colchester United | | 1:1 |
| |
Football League Cup 1977/78, First Round |
| 13.08.1977 | | Aldershot | | Colchester United | | 1:1 |
| |
Football League Cup 1976/77, First Round |
| 30.08.1976 | | Colchester United | | Millwall | | 4:4 aet, pen. 4:5 * |
| |
Football League Cup 1974/75, Fourth Round |
| 13.11.1974 | | Colchester United | | Southampton | | 0:0 |
| |
Football League Cup 1970/71, Second round |
| 09.09.1970 | | Colchester United | | Birmingham City | | 1:1 |
| |
Football League Cup 1969/70, First Round |
| 13.08.1969 | | Colchester United | | Reading | | 1:1 |
| |
Football League Cup 1964/65, First Round |
| 02.09.1964 | | Colchester United | | Torquay United | | 1:1 |
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