Football League Cup 2022/23, Third Round |
 | 08.11.2022 |  | Brentford | – | Gillingham | | 1:1 (1:0),
pen. 5:6 |
| Brentford |
Football League Cup 2022/23, Second Round |
| 23.08.2022 | | Gillingham | – | Exeter City | | 0:0,
pen. 6:5 |
| Gillingham |
Football League Cup 2021/22, Second round |
| 24.08.2021 | | Gillingham | – | Cheltenham Town | | 1:1 (1:1),
pen. 4:5 |
| Gillingham |
Football League Cup 2021/22, First Round |
| 10.08.2021 | | Crawley Town | – | Gillingham | | 2:2 (0:1),
pen. 9:10 |
| Crawley |
Football League Cup 2020/21, Second round |
| 15.09.2020 | | Gillingham | – | Coventry City | | 1:1 (0:0),
pen. 5:4 * |
| Gillingham |
Football League Cup 2019/20, First Round |
| 13.08.2019 | | Gillingham | – | Newport County |  | 2:2 (1:0),
pen. 1:4 |
| Gillingham |
Football League Cup 2018/19, First Round |
| 14.08.2018 | | Millwall | – | Gillingham | | 0:0,
pen. 3:1 |
| London |
Football League Cup 2000/01, Second round |
| 20.09.2000 | | Manchester City | – | Gillingham | | 1:1 (0:0) |
| Manchester |
Football League Cup 1996/97, Third round |
| 22.10.1996 | | Gillingham | – | Coventry City | | 2:2 (0:2) |
| Gillingham |
Football League Cup 1996/97, Second round |
| 17.09.1996 | | Barnsley | – | Gillingham | | 1:1 (0:0) |
| Barnsley |
Football League Cup 1995/96, First Round |
| 15.08.1995 | | Gillingham | – | Bristol Rovers | | 1:1 (0:0) |
| Gillingham |
Football League Cup 1992/93, Second round |
| 23.09.1992 | | Gillingham | – | Southampton | | 0:0 |
| Gillingham |
Football League Cup 1986/87, Second round |
| 07.10.1986 | | Gillingham | – | Oxford United | | 1:1 |
| Gillingham |
Football League Cup 1986/87, First Round |
| 03.09.1986 | | Northampton Town | – | Gillingham | | 2:2 |
| Northampton |
Football League Cup 1985/86, First Round |
| 20.08.1985 | | Southend United | – | Gillingham | | 1:1 |
| |
Football League Cup 1981/82, First Round |
| 15.09.1981 | | Gillingham | – | Colchester United | | 1:1 |
| |
Football League Cup 1980/81, Second round |
| 27.08.1980 | | Blackburn Rovers | – | Gillingham | | 0:0 |
| |
Football League Cup 1979/80, Second round |
| 28.08.1979 | | Gillingham | – | Norwich City | | 1:1 |
| |
Football League Cup 1979/80, First Round |
| 14.08.1979 | | Luton Town | – | Gillingham | | 1:1 |
| |
Football League Cup 1977/78, First Round |
| 13.08.1977 | | Gillingham | – | Wimbledon | | 1:1 |
| |
Football League Cup 1976/77, First Round |
| 14.08.1976 | | Aldershot | – | Gillingham | | 1:1 |
| |
Football League Cup 1975/76, First Round |
| 25.08.1975 | | Gillingham | – | Reading | | 1:1 |
| |
Football League Cup 1974/75, First Round |
| 28.08.1974 | | Bournemouth | – | Gillingham | | 1:1 aet * |
| |
Football League Cup 1974/75, First Round |
| 21.08.1974 | | Gillingham | – | Bournemouth | | 1:1 |
| |
Football League Cup 1971/72, Third round |
| 06.10.1971 | | Gillingham | – | Grimsby Town | | 1:1 |
| |
Football League Cup 1968/69, First Round |
| 14.08.1968 | | Gillingham | – | Orient | | 2:2 |
| |
Football League Cup 1967/68, Second round |
| 13.09.1967 | | Gillingham | – | Torquay United | | 2:2 |
| |
Football League Cup 1966/67, Second round |
| 21.09.1966 | | Gillingham | – | Arsenal | | 1:1 aet * |
| |
Football League Cup 1966/67, Second round |
| 13.09.1966 | | Arsenal | – | Gillingham | | 1:1 |
| London |
Football League Cup 1966/67, First Round |
| 24.08.1966 | | Southend United | – | Gillingham | | 0:0 |
| |
Football League Cup 1963/64, Third round |
| 04.11.1963 | | Bristol Rovers | – | Gillingham | | 1:1 |
| |
Football League Cup 1960/61, Second round |
| 19.10.1960 | | Gillingham | – | Preston North End | | 1:1 |
| |
