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 |
| |
Ukraine
Azerbaijan
Armenia
Belarus
Kazakhstan
Moldova
Uzbekistan
Austria
England
Belgium
Bulgaria
Hungary
Germany
Netherlands
Georgia
Iceland
Spain
Italy
Latvia
Lithuania
Norway
Poland
Portugal
Serbia
Slovenia
France
Croatia
Montenegro
Czech
Sweden
Scotland
Estonia
Argentina
USA
Canada
China
Australia
