Football League Cup 2023/24, Second Round |
| 29.08.2023 | | Luton Town | | Gillingham | | 3:2 (2:0) |
| Luton |
Football League Cup 2022/23, Fourth Round |
| 20.12.2022 | | Wolverhampton Wanderers | | Gillingham | | 2:0 (0:0) |
| Wolverhampton |
Football League Cup 2020/21, Third round |
| 23.09.2020 | | Stoke City | | Gillingham | | 1:0 (1:0) * |
| Stoke-on-Trent |
Football League Cup 2017/18, First Round |
| 08.08.2017 | | Reading | | Gillingham | | 2:0 (0:0) |
| Reading |
Football League Cup 2016/17, Third round |
| 21.09.2016 | | Tottenham Hotspur | | Gillingham | | 5:0 (1:0) |
| London |
Football League Cup 2015/16, Second round |
| 25.08.2015 | | Birmingham City | | Gillingham | | 2:0 (1:0) |
| Birmingham |
Football League Cup 2014/15, Second round |
| 26.08.2014 | | Gillingham | | Newcastle United | | 0:1 (0:1) |
| Gillingham |
Football League Cup 2013/14, First Round |
| 06.08.2013 | | Gillingham | | Bristol City | | 0:2 (0:1) |
| Gillingham |
Football League Cup 2012/13, Second round |
| 28.08.2012 | | Gillingham | | Middlesbrough | | 0:2 (0:1) |
| Gillingham |
Football League Cup 2011/12, First Round |
| 09.08.2011 | | Brighton & Hove Albion | | Gillingham | | 1:0 (0:0) |
| Brighton & Hove |
Football League Cup 2010/11, First Round |
| 10.08.2010 | | Norwich City | | Gillingham | | 4:1 (2:1) |
| Norwich |
Football League Cup 2009/10, Second round |
| 25.08.2009 | | Gillingham | | Blackburn Rovers | | 1:3 (0:1) |
| Gillingham |
Football League Cup 2008/09, First Round |
| 12.08.2008 | | Gillingham | | Colchester United | | 0:1 (0:1) |
| Gillingham |
Football League Cup 2007/08, First Round |
| 14.08.2007 | | Watford | | Gillingham | | 3:0 (2:0) |
| Watford |
Football League Cup 2006/07, First Round |
| 22.08.2006 | | Millwall | | Gillingham | | 2:1 (1:0) |
| London |
Football League Cup 2005/06, Third round |
| 25.10.2005 | | Doncaster Rovers | | Gillingham | | 2:0 (0:0) |
| Doncaster |
Football League Cup 2004/05, First Round |
| 24.08.2004 | | Gillingham | | Northampton Town | | 1:2 (0:2) |
| Gillingham |
Football League Cup 2003/04, Third round |
| 28.10.2003 | | Bolton Wanderers | | Gillingham | | 2:0 (1:0) |
| Bolton |
Football League Cup 2002/03, Third round |
| 06.11.2002 | | Chelsea | | Gillingham | | 2:1 (1:0) |
| London |
Football League Cup 2001/02, Third round |
| 09.10.2001 | | Gillingham | | Southampton | | 0:2 (0:1) |
| Gillingham |
Football League Cup 2000/01, Second round |
| 26.09.2000 | | Gillingham | | Manchester City | | 2:4 aet (1:0, 2:2) |
| Gillingham |
Football League Cup 2000/01, First Round |
| 05.09.2000 | | Torquay United | | Gillingham | | 3:2 (2:1) |
| Torquay |
Football League Cup 1999/00, Second round |
| 21.09.1999 | | Bolton Wanderers | | Gillingham | | 2:0 (2:0) |
| Bolton |
Football League Cup 1999/00, Second round |
| 14.09.1999 | | Gillingham | | Bolton Wanderers | | 1:4 (0:2) |
| Gillingham |
Football League Cup 1998/99, First Round |
| 18.08.1998 | | Gillingham | | Southend United | | 0:1 (0:0) |
| Gillingham |
Football League Cup 1998/99, First Round |
| 11.08.1998 | | Southend United | | Gillingham | | 1:0 (0:0) |
| Southend-on-Sea |
Football League Cup 1997/98, First Round |
| 26.08.1997 | | Birmingham City | | Gillingham | | 3:0 (0:0) |
| Birmingham |
Football League Cup 1997/98, First Round |
| 12.08.1997 | | Gillingham | | Birmingham City | | 0:1 (0:0) |
| Gillingham |
Football League Cup 1996/97, Fourth Round |
| 26.11.1996 | | Ipswich Town | | Gillingham | | 1:0 (0:0) |
| Ipswich |
Football League Cup 1995/96, First Round |
| 23.08.1995 | | Bristol Rovers | | Gillingham | | 4:2 (1:1) |
| Bath |
Football League Cup 1994/95, First Round |
| 23.08.1994 | | Reading | | Gillingham | | 3:0 (0:0) |
| Reading |
Football League Cup 1994/95, First Round |
| 16.08.1994 | | Gillingham | | Reading | | 0:1 (0:0) |
| Gillingham |
Football League Cup 1993/94, First Round |
| 25.08.1993 | | Brighton & Hove Albion | | Gillingham | | 2:0 (1:0) |
| Hove |
Football League Cup 1992/93, Second round |
| 07.10.1992 | | Southampton | | Gillingham | | 3:0 (1:0) |
| Southampton |
Football League Cup 1991/92, First Round |
| 27.08.1991 | | Gillingham | | Portsmouth | | 3:4 (1:2) |
| Gillingham |
Football League Cup 1991/92, First Round |
| 20.08.1991 | | Portsmouth | | Gillingham | | 2:1 (1:0) |
| Portsmouth |
Football League Cup 1990/91, First Round |
| 04.09.1990 | | Shrewsbury Town | | Gillingham | | 2:0 |
| Shrewsbury |
Football League Cup 1989/90, First Round |
| 29.08.1989 | | Leyton Orient | | Gillingham | | 3:0 |
| London |
Football League Cup 1989/90, First Round |
| 22.08.1989 | | Gillingham | | Leyton Orient | | 1:4 |
| Gillingham |
Football League Cup 1988/89, Second round |
| 11.10.1988 | | Gillingham | | Millwall | | 1:3 |
| Gillingham |
Football League Cup 1988/89, Second round |
| 27.09.1988 | | Millwall | | Gillingham | | 3:0 |
| London |
Football League Cup 1987/88, Second round |
| 06.10.1987 | | Gillingham | | Stoke City | | 0:1 |
| Gillingham |
Football League Cup 1987/88, Second round |
| 22.09.1987 | | Stoke City | | Gillingham | | 2:0 |
| Stoke-on-Trent |
Football League Cup 1987/88, First Round |
| 26.08.1987 | | Brighton & Hove Albion | | Gillingham | | 1:0 aet (1:0), pen. 4:5 |
| Hove |
Football League Cup 1986/87, Second round |
| 24.09.1986 | | Oxford United | | Gillingham | | 6:0 |
| Oxford |
Football League Cup 1985/86, Second round |
| 08.10.1985 | | Portsmouth | | Gillingham | | 2:1 |
| |
Football League Cup 1985/86, Second round |
| 24.09.1985 | | Gillingham | | Portsmouth | | 1:3 |
| |
Football League Cup 1984/85, Second round |
| 10.10.1984 | | Leeds United | | Gillingham | | 3:2 |
| |
Football League Cup 1984/85, Second round |
| 25.09.1984 | | Gillingham | | Leeds United | | 1:2 |
| |
Football League Cup 1983/84, First Round |
| 13.09.1983 | | Chelsea | | Gillingham | | 4:0 |
| London |
Football League Cup 1983/84, First Round |
| 30.08.1983 | | Gillingham | | Chelsea | | 1:2 |
| |
Football League Cup 1982/83, Third round |
| 09.11.1982 | | Gillingham | | Tottenham Hotspur | | 2:4 |
| |
Football League Cup 1982/83, Second round |
| 26.10.1982 | | Oldham Athletic | | Gillingham | | 1:0 |
| |
Football League Cup 1982/83, First Round |
| 14.09.1982 | | Leyton Orient | | Gillingham | | 2:0 |
| |
Football League Cup 1981/82, First Round |
| 01.09.1981 | | Colchester United | | Gillingham | | 2:0 |
| |
Football League Cup 1980/81, Second round |
| 02.09.1980 | | Gillingham | | Blackburn Rovers | | 1:2 aet |
| |
Football League Cup 1979/80, Second round |
| 05.09.1979 | | Norwich City | | Gillingham | | 4:2 |
| |
Football League Cup 1978/79, First Round |
| 15.08.1978 | | Gillingham | | Reading | | 1:2 |
| |
Football League Cup 1978/79, First Round |
| 12.08.1978 | | Reading | | Gillingham | | 3:1 |
| |
Football League Cup 1977/78, First Round |
| 16.08.1977 | | Wimbledon | | Gillingham | | 3:1 |
| |
Football League Cup 1976/77, Second round |
| 01.09.1976 | | Gillingham | | Newcastle United | | 1:2 |
| |
Football League Cup 1975/76, Second round |
| 09.09.1975 | | Carlisle United | | Gillingham | | 2:0 |
| |
Football League Cup 1974/75, First Round |
| 03.09.1974 | | Gillingham | | Bournemouth | | 1:2 aet * |
| |
Football League Cup 1973/74, Second round |
| 10.10.1973 | | Gillingham | | Carlisle United | | 1:2 |
| |
Football League Cup 1972/73, Second round |
| 05.09.1972 | | Gillingham | | Millwall | | 0:2 |
| |
Football League Cup 1971/72, Third round |
| 12.10.1971 | | Grimsby Town | | Gillingham | | 1:0 * |
| |
Football League Cup 1970/71, First Round |
| 19.08.1970 | | Gillingham | | Luton Town | | 0:1 |
| |
Football League Cup 1969/70, Second round |
| 03.09.1969 | | Blackpool | | Gillingham | | 3:1 |
| |
Football League Cup 1968/69, First Round |
| 20.08.1968 | | Orient | | Gillingham | | 3:0 * |
| |
Football League Cup 1967/68, Second round |
| 20.09.1967 | | Torquay United | | Gillingham | | 2:0 * |
| |
Football League Cup 1966/67, Second round |
| 28.09.1966 | | Arsenal | | Gillingham | | 5:0 * |
| London |
Football League Cup 1965/66, Second round |
| 22.09.1965 | | Blackpool | | Gillingham | | 5:2 |
| |
Football League Cup 1964/65, First Round |
| 02.09.1964 | | Exeter City | | Gillingham | | 2:0 |
| |
Football League Cup 1963/64, Fourth Round |
| 27.11.1963 | | Leicester City | | Gillingham | | 3:1 |
| |
Football League Cup 1962/63, First Round |
| 05.09.1962 | | Newport County | | Gillingham | | 2:1 |
| |
Football League Cup 1961/62, First Round |
| 11.09.1961 | | Nottingham Forest | | Gillingham | | 4:1 |
| |
Football League Cup 1960/61, Second round |
| 25.10.1960 | | Preston North End | | Gillingham | | 3:0 * |
| |