FA Cup 2023/24, Third Round Proper |
 | 06.01.2024 | | Gillingham | – | Sheffield United | | 0:4 (0:2) |
| Gillingham |
FA Cup 2022/23, Third Round Proper |
| 07.01.2023 | | Gillingham | – | Leicester City | | 0:1 (0:0) |
| Gillingham |
FA Cup 2021/22, First Round Proper |
| 16.11.2021 | | Cheltenham Town | – | Gillingham | | 1:0 (1:0) * |
| Cheltenham |
FA Cup 2020/21, Second Round Proper |
| 28.11.2020 | | Gillingham | – | Exeter City | | 2:3 (1:3) * |
| Gillingham |
FA Cup 2019/20, Third Round Proper |
| 05.01.2020 | | Gillingham | – | West Ham United | | 0:2 (0:0) |
| Gillingham |
FA Cup 2018/19, Fourth Round Proper |
| 26.01.2019 | | Swansea City | – | Gillingham | | 4:1 (2:0) |
| Swansea |
FA Cup 2017/18, Second Round Proper |
| 19.12.2017 | | Carlisle United | – | Gillingham | | 3:1 (2:0) * |
| Carlisle |
FA Cup 2016/17, First Round Proper |
| 16.11.2016 | | Brackley Town | – | Gillingham | | 4:3 aet
(2:1, 2:2) * |
| Brackley |
FA Cup 2015/16, First Round Proper |
| 07.11.2015 | | Stevenage | – | Gillingham | | 3:0 (2:0) |
| Stevenage |
FA Cup 2014/15, First Round Proper |
| 08.11.2014 | | Gillingham | – | Bristol City | | 1:2 (0:1) |
| Gillingham |
FA Cup 2013/14, First Round Proper |
| 18.11.2013 | | Brackley Town | – | Gillingham | | 1:0 (1:0) * |
| Brackley |
FA Cup 2012/13, Second Round Proper |
| 01.12.2012 | | Preston North End | – | Gillingham | | 2:0 (2:0) |
| Preston |
FA Cup 2011/12, Third Round Proper |
| 07.01.2012 | | Gillingham | – | Stoke City | | 1:3 (1:2) |
| Gillingham |
FA Cup 2010/11, First Round Proper |
| 06.11.2010 | | Gillingham | – | Dover Athletic | | 0:2 (0:2) |
| Gillingham |
FA Cup 2009/10, Third Round Proper |
| 19.01.2010 | | Accrington Stanley | – | Gillingham | | 1:0 (0:0) |
| Accrington |
FA Cup 2008/09, Third Round Proper |
| 04.01.2009 | | Gillingham | – | Aston Villa | | 1:2 (0:1) |
| Gillingham |
FA Cup 2007/08, First Round Proper |
| 10.11.2007 | | Barnet | – | Gillingham | | 2:1 (0:1) |
| London |
FA Cup 2006/07, Second Round Proper |
| 03.12.2006 | | Bristol City | – | Gillingham | | 4:3 (3:0) |
| Bristol |
FA Cup 2005/06, First Round Proper |
| 05.11.2005 | | Burscough | – | Gillingham | | 3:2 (1:0) |
| Burscough |
FA Cup 2004/05, Third Round Proper |
| 08.01.2005 | | Portsmouth | – | Gillingham | | 1:0 (0:0) |
| Portsmouth |
FA Cup 2003/04, Fourth Round Proper |
| 24.01.2004 | | Burnley | – | Gillingham | | 3:1 (2:0) |
| Burnley |
FA Cup 2002/03, Fourth Round Proper |
| 04.02.2003 | | Leeds United | – | Gillingham | | 2:1 (1:0) * |
| Leeds |
FA Cup 2001/02, Fifth Round Proper |
| 16.02.2002 | | Arsenal | – | Gillingham | | 5:2 (1:0) |
| London |
FA Cup 2000/01, Fourth Round Proper |
| 28.01.2001 | | Gillingham | – | Chelsea | | 2:4 (0:3) |
| Gillingham |
FA Cup 1999/00, Sixth Round Proper |
| 20.02.2000 | | Chelsea | – | Gillingham | | 5:0 (1:0) |
| London |
FA Cup 1998/99, First Round Proper |
| 14.11.1998 | | Oldham Athletic | – | Gillingham | | 2:0 (2:0) |
| Oldham |
FA Cup 1997/98, First Round Proper |
| 25.11.1997 | | Gillingham | – | Bristol Rovers | | 0:2 (0:2) * |
| Gillingham |
FA Cup 1996/97, Third Round Proper |
| 21.01.1997 | | Gillingham | – | Derby County | | 0:2 (0:0) |
| Gillingham |
FA Cup 1995/96, Third Round Proper |
| 06.01.1996 | | Reading | – | Gillingham | | 3:1 (0:1) |
| Reading |
FA Cup 1994/95, Third Round Proper |
| 07.01.1995 | | Gillingham | – | Sheffield Wednesday | | 1:2 (1:2) |
| Gillingham |
FA Cup 1993/94, Second Round Proper |
| 04.12.1993 | | Plymouth Argyle | – | Gillingham | | 2:0 (1:0) |
| Plymouth |
FA Cup 1992/93, Third Round Proper |
| 13.01.1993 | | Huddersfield Town | – | Gillingham | | 2:1 (1:0) * |
| Huddersfield |
FA Cup 1991/92, First Round Proper |
| 26.11.1991 | | Gillingham | – | Brentford | | 1:3 * |
| Gillingham |
FA Cup 1990/91, First Round Proper |
| 17.11.1990 | | Bournemouth | – | Gillingham | | 2:1 |
| Bournemouth |
FA Cup 1989/90, First Round Proper |
| 22.11.1989 | | Welling United | – | Gillingham | | 1:0 * |
| London |
FA Cup 1988/89, First Round Proper |
| 23.11.1988 | | Peterborough United | – | Gillingham | | 1:0 aet
(0:0, 0:0) * |
| Peterborough |
FA Cup 1987/88, Third Round Proper |
| 09.01.1988 | | Gillingham | – | Birmingham City | | 0:3 (0:2) |
| Gillingham |
FA Cup 1986/87, Third Round Proper |
| 19.01.1987 | | Wigan Athletic | – | Gillingham | | 2:1 (1:0) |
| Wigan |
FA Cup 1985/86, Third Round Proper |
| 13.01.1986 | | Derby County | – | Gillingham | | 3:1 * |
| |
FA Cup 1984/85, Fourth Round Proper |
| 26.01.1985 | | Ipswich Town | – | Gillingham | | 3:2 |
| |
FA Cup 1983/84, Fourth Round Proper |
| 06.02.1984 | | Gillingham | – | Everton | | 0:3 * |
| Gillingham |
FA Cup 1982/83, Second Round Proper |
| 14.12.1982 | | Northampton Town | – | Gillingham | | 3:2 * |
| |
FA Cup 1981/82, Fourth Round Proper |
| 23.01.1982 | | Gillingham | – | West Bromwich Albion | | 0:1 |
| |
FA Cup 1980/81, Second Round Proper |
| 22.12.1980 | | Gillingham | – | Maidstone United | | 0:2 * |
| |
FA Cup 1979/80, First Round Proper |
| 27.11.1979 | | Wimbledon | – | Gillingham | | 4:2 * |
| |
FA Cup 1978/79, First Round Proper |
| 28.11.1978 | | Gillingham | – | Reading | | 1:2 * |
| |
FA Cup 1977/78, Second Round Proper |
| 20.12.1977 | | Peterborough United | – | Gillingham | | 2:0 * |
| |
FA Cup 1976/77, First Round Proper |
| 20.11.1976 | | Gillingham | – | Watford | | 0:1 |
| Gillingham |
FA Cup 1975/76, Second Round Proper |
| 13.12.1975 | | Gillingham | – | Brighton & Hove Albion | | 0:1 |
| |
FA Cup 1974/75, First Round Proper |
| 26.11.1974 | | Hereford United | – | Gillingham | | 1:0 |
| |
FA Cup 1973/74, First Round Proper |
| 24.11.1973 | | Cambridge United | – | Gillingham | | 3:2 |
| |
FA Cup 1972/73, First Round Proper |
| 18.11.1972 | | Gillingham | – | Reading | | 1:2 |
| |
FA Cup 1971/72, Third Round Proper |
| 15.01.1972 | | Swansea City | – | Gillingham | | 1:0 |
| |
FA Cup 1970/71, First Round Proper |
| 21.11.1970 | | Brentford | – | Gillingham | | 2:1 |
| |
FA Cup 1969/70, Fifth Round Proper |
| 07.02.1970 | | Watford | – | Gillingham | | 2:1 (0:0) |
| |
FA Cup 1968/69, Second Round Proper |
| 07.12.1968 | | Luton Town | – | Gillingham | | 3:1 |
| |
FA Cup 1967/68, First Round Proper |
| 18.12.1967 | | Newport County | – | Gillingham | | 3:0 |
| |
FA Cup 1966/67, Second Round Proper |
| 07.01.1967 | | Walsall | – | Gillingham | | 3:1 |
| |
FA Cup 1965/66, First Round Proper |
| 13.11.1965 | | Gillingham | – | Folkestone | | 1:2 |
| |
FA Cup 1964/65, Second Round Proper |
| 05.12.1964 | | Luton Town | – | Gillingham | | 1:0 |
| |
FA Cup 1963/64, First Round Proper |
| 16.11.1963 | | Queens Park Rangers | – | Gillingham | | 4:1 |
| |
FA Cup 1962/63, Third Round Proper |
| 27.02.1963 | | Gillingham | – | Port Vale | | 2:4 |
| |
FA Cup 1961/62, First Round Proper |
| 04.11.1961 | | Coventry City | – | Gillingham | | 2:0 |
| |
FA Cup 1960/61, Third Round Proper |
| 07.01.1961 | | Gillingham | – | Leyton Orient | | 2:6 |
| |
FA Cup 1959/60, Third Round Proper |
| 09.01.1960 | | Gillingham | – | Swansea Town | | 1:4 |
| |
FA Cup 1958/59, First Round Proper |
| 19.11.1958 | | Gillingham | – | Plymouth Argyle | | 1:4 * |
| |
FA Cup 1957/58, Third Round Proper |
| 04.01.1958 | | Nottingham Forest | – | Gillingham | | 2:0 |
| |
FA Cup 1956/57, Second Round Proper |
| 08.12.1956 | | Gillingham | – | Newport County | | 1:2 |
| |
FA Cup 1955/56, First Round Proper |
| 24.11.1955 | | Shrewsbury Town | – | Gillingham | | 4:1 * |
| |
FA Cup 1954/55, Second Round Proper |
| 13.12.1954 | | Reading | – | Gillingham | | 5:3 * |
| |
FA Cup 1953/54, First Round Proper |
| 21.11.1953 | | Walthamstow Avenue | – | Gillingham | | 1:0 |
| |
FA Cup 1952/53, Second Round Proper |
| 06.12.1952 | | Stockport County | – | Gillingham | | 3:1 |
| |
FA Cup 1951/52, Second Round Proper |
| 15.12.1951 | | Gillingham | – | Rochdale | | 0:3 |
| |
FA Cup 1950/51, Second Round Proper |
| 18.12.1950 | | Bristol Rovers | – | Gillingham | | 2:1 * |
| London |
FA Cup 1949/50, Second Round Proper |
| 10.12.1949 | | Yeovil Town | – | Gillingham | | 3:1 |
| |
FA Cup 1948/49, Fourth Qualifying Round |
| | | Romford | – | Gillingham | | 2:1 |
| |
FA Cup 1947/48, Third Round Proper |
| 17.01.1948 | | Queens Park Rangers | – | Gillingham | | 3:1 * |
| |
FA Cup 1946/47, Third Round Proper |
| 11.01.1947 | | Swansea Town | – | Gillingham | | 4:1 |
| |
FA Cup 1945/46, Fourth Qualifying Round |
| | | Gillingham | – | Sutton United | | 3:9 |
| |
FA Cup 1937/38, First Round Proper |
| 27.11.1937 | | Gillingham | – | Swindon Town | | 3:4 |
| |
FA Cup 1936/37, Second Round Proper |
| 12.12.1936 | | Wrexham | – | Gillingham | | 2:0 |
| |
FA Cup 1935/36, Second Round Proper |
| 14.12.1935 | | Crewe Alexandra | – | Gillingham | | 2:1 |
| |
FA Cup 1934/35, First Round Proper |
| 24.11.1934 | | Bristol City | – | Gillingham | | 2:0 |
| |
FA Cup 1933/34, Second Round Proper |
| 09.12.1933 | | Charlton Athletic | – | Gillingham | | 1:0 |
| |
FA Cup 1932/33, Second Round Proper |
| 14.12.1932 | | Gillingham | – | Bristol Rovers | | 1:3 * |
| |
FA Cup 1931/32, First Round Proper |
| 28.11.1931 | | Bristol Rovers | – | Gillingham | | 5:1 |
| |
FA Cup 1930/31, Second Round Proper |
| 13.12.1930 | | Gillingham | – | Aldershot | | 1:3 |
| |
FA Cup 1929/30, First Round Proper |
| 30.11.1929 | | Gillingham | – | Margate | | 0:2 |
| |
FA Cup 1928/29, First Round Proper |
| 28.11.1928 | | Torquay United | – | Gillingham | | 5:1 * |
| |
FA Cup 1927/28, Third Round Proper |
| 14.01.1928 | | Stoke City | – | Gillingham | | 6:1 |
| |
FA Cup 1926/27, Second Round Proper |
| 15.12.1926 | | Brentford | – | Gillingham | | 1:0 * |
| |
FA Cup 1925/26, Second Round Proper |
| 12.12.1925 | | Southend United | – | Gillingham | | 1:0 |
| |
FA Cup 1923/24, First Round Proper |
| 16.01.1924 | | Gillingham | – | Cardiff City | | 0:2 * |
| |
FA Cup 1921/22, First Round Proper |
| 07.01.1922 | | Gillingham | – | Oldham Athletic | | 1:3 |
| |
FA Cup 1919/20, First Round Proper |
| 17.01.1920 | | West Stanley | – | Gillingham | | 3:1 |
| |
FA Cup 1914/15, First Round Proper |
| 09.01.1915 | | Rochdale | – | Gillingham | | 2:0 |
| |
FA Cup 1913/14, Second Round Proper |
| 31.01.1914 | | Liverpool | – | Gillingham | | 2:0 |
| |
FA Cup 1912/13, First Round Proper |
| 16.01.1913 | | Barnsley | – | Gillingham | | 3:1 * |
| |
FA Cup 1910/11, First Round Proper |
| 14.01.1911 | | New Brompton | – | Bradford City | | 0:1 |
| |
FA Cup 1909/10, First Round Proper |
| 24.01.1910 | | Leyton | – | New Brompton | | 1:0 * |
| |
FA Cup 1907/08, Second Round Proper |
| 05.02.1908 | | New Brompton | – | Manchester City | | 1:2 * |
| |
FA Cup 1906/07, Second Round Proper |
| 02.02.1907 | | Bury | – | New Brompton | | 1:0 |
| |
FA Cup 1905/06, Second Round Proper |
| 07.02.1906 | | Southampton | – | New Brompton | | 1:0 * |
| |
FA Cup 1903/04, Intermediate Round |
| 16.12.1903 | | Bristol City | – | New Brompton | | 5:2 * |
| |
FA Cup 1902/03, Intermediate Round |
| 13.12.1902 | | Glossop | – | New Brompton | | 2:1 |
| |
FA Cup 1901/02, Intermediate Round |
| 14.12.1901 | | Walsall | – | New Brompton | | 2:0 |
| |
FA Cup 1898/99, First Round Proper |
| 28.01.1899 | | New Brompton | – | Southampton | | 0:1 |
| |
