Football League Cup 2023/24, First Round |
 | 08.08.2023 |  | Gillingham | – | Southampton | | 3:1 (1:0) |
| Gillingham |
Football League Cup 2022/23, First Round |
| 09.08.2022 | | AFC Wimbledon | – | Gillingham | | 0:2 (0:0) |
| London |
Football League Cup 2020/21, First Round |
| 05.09.2020 | | Gillingham | – | Southend United | | 1:0 (1:0) * |
| Gillingham |
Football League Cup 2016/17, Second round |
| 23.08.2016 | | Watford | – | Gillingham | | 1:2 aet
(0:0, 1:1) |
| Watford |
Football League Cup 2016/17, First Round |
| 09.08.2016 | | Southend United | – | Gillingham | | 1:3 (1:0) |
| Southend-on-Sea |
Football League Cup 2015/16, First Round |
| 11.08.2015 | | Plymouth Argyle | – | Gillingham | | 1:2 (0:0) |
| Plymouth |
Football League Cup 2014/15, First Round |
| 12.08.2014 | | Yeovil Town | – | Gillingham | | 1:2 (0:1) |
| Yeovil |
Football League Cup 2012/13, First Round |
| 14.08.2012 | | Bristol City | – | Gillingham | | 1:2 (0:1) |
| Bristol |
Football League Cup 2009/10, First Round |
| 11.08.2009 | | Gillingham | – | Plymouth Argyle | | 2:1 (2:0) |
| Gillingham |
Football League Cup 2005/06, Second round |
| 20.09.2005 | | Gillingham | – | Portsmouth | | 3:2 aet
(1:1, 2:2) |
| Gillingham |
Football League Cup 2005/06, First Round |
| 23.08.2005 | | Gillingham | – | Oxford United | | 1:0 (0:0) |
| Gillingham |
Football League Cup 2003/04, Second round |
| 23.09.2003 | | Stoke City | – | Gillingham | | 0:2 (0:1) |
| Stoke-on-Trent |
Football League Cup 2003/04, First Round |
| 12.08.2003 | | Cambridge United | – | Gillingham | | 1:2 (1:0) |
| Cambridge |
Football League Cup 2002/03, Second round |
| 01.10.2002 | | Stockport County | – | Gillingham | | 1:2 aet
(1:1, 1:1) |
| Stockport |
Football League Cup 2002/03, First Round |
| 10.09.2002 | | Torquay United | – | Gillingham | | 0:1 (0:0) |
| Torquay |
Football League Cup 2001/02, Second round |
| 11.09.2001 | | Gillingham | – | Millwall | | 2:1 (1:0) |
| Gillingham |
Football League Cup 2001/02, First Round |
| 21.08.2001 | | Oxford United | – | Gillingham | | 1:2 aet
(1:0, 1:1) |
| Oxford |
Football League Cup 2000/01, First Round |
| 22.08.2000 | | Gillingham | – | Torquay United | | 2:0 (1:0) |
| Gillingham |
Football League Cup 1999/00, First Round |
| 24.08.1999 | | Gillingham | – | Brighton & Hove Albion | | 2:0 (2:0) |
| Gillingham |
Football League Cup 1999/00, First Round |
| 11.08.1999 | | Brighton & Hove Albion | – | Gillingham | | 0:2 (0:1) |
| Brighton & Hove |
Football League Cup 1996/97, Third round |
| 13.11.1996 | | Coventry City | – | Gillingham | | 0:1 (0:0) * |
| Coventry |
Football League Cup 1996/97, Second round |
| 24.09.1996 | | Gillingham | – | Barnsley | | 1:0 aet
(0:0) |
| Gillingham |
Football League Cup 1996/97, First Round |
| 03.09.1996 | | Gillingham | – | Swansea City |  | 2:0 (1:0) |
| Gillingham |
Football League Cup 1996/97, First Round |
| 20.08.1996 | | Swansea City | – | Gillingham | | 0:1 (0:0) |
| Swansea |
Football League Cup 1993/94, First Round |
| 17.08.1993 | | Gillingham | – | Brighton & Hove Albion | | 1:0 (0:0) |
| Gillingham |
Football League Cup 1992/93, First Round |
| 09.09.1992 | | Northampton Town | – | Gillingham | | 0:2 (0:0) |
| Northampton |
Football League Cup 1992/93, First Round |
| 18.08.1992 | | Gillingham | – | Northampton Town | | 2:1 (1:0) |
| Gillingham |
Football League Cup 1990/91, First Round |
| 28.08.1990 | | Gillingham | – | Shrewsbury Town | | 1:0 |
| Gillingham |
Football League Cup 1988/89, First Round |
| 06.09.1988 | | Gillingham | – | Cambridge United | | 3:1 |
| Gillingham |
Football League Cup 1988/89, First Round |
| 30.08.1988 | | Cambridge United | – | Gillingham | | 1:2 |
| Cambridge |
Football League Cup 1987/88, First Round |
| 18.08.1987 | | Gillingham | – | Brighton & Hove Albion | | 1:0 |
| Gillingham |
Football League Cup 1986/87, First Round |
| 25.08.1986 | | Gillingham | – | Northampton Town | | 1:0 |
| Gillingham |
Football League Cup 1985/86, First Round |
| 03.09.1985 | | Gillingham | – | Southend United | | 2:0 |
| |
Football League Cup 1984/85, First Round |
| 04.09.1984 | | Colchester United | – | Gillingham | | 0:2 |
| |
Football League Cup 1984/85, First Round |
| 28.08.1984 | | Gillingham | – | Colchester United | | 3:2 |
| |
Football League Cup 1982/83, Second round |
| 05.10.1982 | | Gillingham | – | Oldham Athletic | | 2:0 |
| |
Football League Cup 1982/83, First Round |
| 31.08.1982 | | Gillingham | – | Leyton Orient | | 3:0 |
| |
Football League Cup 1980/81, First Round |
| 12.08.1980 | | Gillingham | – | Colchester United | | 2:1 |
| |
Football League Cup 1980/81, First Round |
| 09.08.1980 | | Colchester United | – | Gillingham | | 0:2 |
| |
Football League Cup 1979/80, First Round |
| 11.08.1979 | | Gillingham | – | Luton Town | | 3:0 |
| |
Football League Cup 1976/77, First Round |
| 18.08.1976 | | Gillingham | – | Aldershot | | 2:0 |
| |
Football League Cup 1975/76, First Round |
| 20.08.1975 | | Reading | – | Gillingham | | 0:1 |
| |
Football League Cup 1973/74, First Round |
| 29.08.1973 | | Gillingham | – | Colchester United | | 4:2 |
| |
Football League Cup 1972/73, First Round |
| 16.08.1972 | | Gillingham | – | Colchester United | | 1:0 |
| |
Football League Cup 1971/72, Second round |
| 08.09.1971 | | Notts County | – | Gillingham | | 1:2 |
| |
Football League Cup 1971/72, First Round |
| 18.08.1971 | | Gillingham | – | Reading | | 4:0 |
| |
Football League Cup 1969/70, First Round |
| 13.08.1969 | | Aldershot | – | Gillingham | | 0:1 |
| |
Football League Cup 1967/68, First Round |
| 22.08.1967 | | Orient | – | Gillingham | | 1:3 |
| |
Football League Cup 1966/67, First Round |
| 31.08.1966 | | Gillingham | – | Southend United | | 2:0 aet * |
| |
Football League Cup 1963/64, Third round |
| 06.11.1963 | | Gillingham | – | Bristol Rovers | | 3:1 * |
| |
Football League Cup 1963/64, Second round |
| 25.09.1963 | | Gillingham | – | Bury | | 3:0 |
| |
Football League Cup 1963/64, First Round |
| 04.09.1963 | | Gillingham | – | Bristol City | | 4:2 |
| |
