FA Cup 2023/24, Second Round Proper |
| 02.12.2023 | | Gillingham | | Charlton Athletic | | 2:0 (2:0) |
| Gillingham |
FA Cup 2023/24, First Round Proper |
| 04.11.2023 | | Hereford | | Gillingham | | 0:2 (0:1) |
| Hereford |
FA Cup 2022/23, Second Round Proper |
| 08.12.2022 | | Gillingham | | Dagenham & Redbridge | | 3:2 (1:1) * |
| Gillingham |
FA Cup 2022/23, First Round Proper |
| 15.11.2022 | | Gillingham | | AFC Fylde | | 1:0 (1:0) * |
| Gillingham |
FA Cup 2020/21, First Round Proper |
| 07.11.2020 | | Gillingham | | Woking | | 3:2 (0:1) * |
| Gillingham |
FA Cup 2019/20, Second Round Proper |
| 01.12.2019 | | Gillingham | | Doncaster Rovers | | 3:0 (2:0) |
| Gillingham |
FA Cup 2019/20, First Round Proper |
| 19.11.2019 | | Gillingham | | Sunderland | | 1:0 aet (0:0, 0:0) * |
| Gillingham |
FA Cup 2018/19, Third Round Proper |
| 05.01.2019 | | Gillingham | | Cardiff City | | 1:0 (0:0) |
| Gillingham |
FA Cup 2018/19, Second Round Proper |
| 02.12.2018 | | Slough Town | | Gillingham | | 0:1 (0:0) |
| Slough |
FA Cup 2018/19, First Round Proper |
| 21.11.2018 | | Hartlepool United | | Gillingham | | 3:4 aet (2:0, 2:2) * |
| Hartlepool |
FA Cup 2017/18, First Round Proper |
| 04.11.2017 | | Gillingham | | Leyton Orient | | 2:1 (1:0) |
| Gillingham |
FA Cup 2012/13, First Round Proper |
| 03.11.2012 | | Gillingham | | Scunthorpe United | | 4:0 (0:0) |
| Gillingham |
FA Cup 2011/12, Second Round Proper |
| 03.12.2011 | | Leyton Orient | | Gillingham | | 0:1 (0:1) |
| London |
FA Cup 2011/12, First Round Proper |
| 22.11.2011 | | Gillingham | | A.F.C. Bournemouth | | 3:2 (1:0) * |
| Gillingham |
FA Cup 2009/10, Second Round Proper |
| 28.11.2009 | | Gillingham | | Burton Albion | | 1:0 (0:0) |
| Gillingham |
FA Cup 2009/10, First Round Proper |
| 07.11.2009 | | Gillingham | | Southend United | | 3:0 (2:0) |
| Gillingham |
FA Cup 2008/09, Second Round Proper |
| 09.12.2008 | | Stockport County | | Gillingham | | 1:2 (1:2) * |
| Stockport |
FA Cup 2008/09, First Round Proper |
| 08.11.2008 | | Bury | | Gillingham | | 0:1 (0:0) |
| Bury |
FA Cup 2006/07, First Round Proper |
| 11.11.2006 | | Gillingham | | Bromley | | 4:1 (1:0) |
| Gillingham |
FA Cup 2003/04, Third Round Proper |
| 03.01.2004 | | Gillingham | | Charlton Athletic | | 3:2 (3:1) |
| Gillingham |
FA Cup 2002/03, Third Round Proper |
| 07.01.2003 | | Gillingham | | Sheffield Wednesday | | 4:1 (3:1) |
| Gillingham |
FA Cup 2001/02, Fourth Round Proper |
| 05.02.2002 | | Gillingham | | Bristol Rovers | | 1:0 (1:0) |
| Gillingham |
FA Cup 2001/02, Third Round Proper |
| 05.01.2002 | | Wolverhampton Wanderers | | Gillingham | | 0:1 (0:0) |
| Wolverhampton |
FA Cup 2000/01, Third Round Proper |
| 06.01.2001 | | AFC Bournemouth | | Gillingham | | 2:3 (1:2) |
| Bournemouth |
FA Cup 1999/00, Fifth Round Proper |
| 29.01.2000 | | Gillingham | | Sheffield Wednesday | | 3:1 (0:1) |
| Gillingham |
FA Cup 1999/00, Fourth Round Proper |
| 11.01.2000 | | Gillingham | | Bradford City | | 3:1 (1:0) |
| Gillingham |
FA Cup 1999/00, Third Round Proper |
| 08.01.2000 | | Gillingham | | Walsall | | 2:1 aet (1:1, 1:1) * |
| Gillingham |
FA Cup 1999/00, First Round Proper |
| 09.11.1999 | | Gillingham | | Cheltenham Town | | 3:2 (2:0) * |
| Gillingham |
FA Cup 1996/97, Second Round Proper |
| 07.12.1996 | | Cardiff City | | Gillingham | | 0:2 (0:1) |
| Cardiff |
FA Cup 1996/97, First Round Proper |
| 16.11.1996 | | Gillingham | | Hereford United | | 1:0 (1:0) |
| Gillingham |
FA Cup 1995/96, Second Round Proper |
| 02.12.1995 | | Gillingham | | Hitchin Town | | 3:0 (0:0) |
| Gillingham |
FA Cup 1995/96, First Round Proper |
| 21.11.1995 | | Gillingham | | Wycombe Wanderers | | 1:0 (1:0) * |
| Gillingham |
FA Cup 1994/95, Second Round Proper |
| 13.12.1994 | | Fulham | | Gillingham | | 1:2 aet (0:1, 1:1) * |
| London |
FA Cup 1994/95, First Round Proper |
| 11.11.1994 | | Heybridge Swifts | | Gillingham | | 0:2 |
| Heybridge |
FA Cup 1993/94, First Round Proper |
| 30.11.1993 | | Gillingham | | Yeading | | 3:1 (3:0) * |
| Gillingham |
FA Cup 1992/93, Second Round Proper |
| 16.12.1992 | | Colchester United | | Gillingham | | 2:3 (0:3) * |
| Colchester |
FA Cup 1992/93, First Round Proper |
| 14.11.1992 | | Gillingham | | Kettering Town | | 3:2 (2:1) |
| Gillingham |
FA Cup 1987/88, Second Round Proper |
| 05.12.1987 | | Gillingham | | Walsall | | 2:1 (2:1) |
| Gillingham |
FA Cup 1987/88, First Round Proper |
| 14.11.1987 | | Gillingham | | Fulham | | 2:1 (2:0) |
| Gillingham |
FA Cup 1986/87, Second Round Proper |
| 06.12.1986 | | Gillingham | | Chelmsford City | | 2:0 (1:0) |
| Gillingham |
FA Cup 1986/87, First Round Proper |
| 15.11.1986 | | Kettering Town | | Gillingham | | 0:3 (0:3) |
| Kettering |
FA Cup 1985/86, Second Round Proper |
| 07.12.1985 | | Gillingham | | Bognor Regis Town | | 6:1 |
| |
FA Cup 1985/86, First Round Proper |
| 16.11.1985 | | Gillingham | | Northampton Town | | 3:0 |
| |
FA Cup 1984/85, Third Round Proper |
| 21.01.1985 | | Gillingham | | Cardiff City | | 2:1 |
| |
FA Cup 1984/85, Second Round Proper |
| 08.12.1984 | | Colchester United | | Gillingham | | 0:5 |
| |
FA Cup 1984/85, First Round Proper |
| 17.11.1984 | | Gillingham | | Windsor & Eton | | 2:1 |
| |
FA Cup 1983/84, Third Round Proper |
| 07.01.1984 | | Gillingham | | Brentford | | 5:3 |
| |
FA Cup 1983/84, Second Round Proper |
| 10.12.1983 | | Gillingham | | Chelmsford City | | 6:1 |
| |
FA Cup 1983/84, First Round Proper |
| 19.11.1983 | | AP Leamington | | Gillingham | | 0:1 |
| |
FA Cup 1982/83, First Round Proper |
| 20.11.1982 | | Gillingham | | Dagenham | | 1:0 |
| |
FA Cup 1981/82, Third Round Proper |
| 05.01.1982 | | Gillingham | | Oldham Athletic | | 2:1 |
| |
FA Cup 1981/82, Second Round Proper |
| 02.01.1982 | | Gillingham | | Barking | | 3:1 * |
| |
FA Cup 1981/82, First Round Proper |
| 24.11.1981 | | Gillingham | | Plymouth Argyle | | 1:0 * |
| |
FA Cup 1980/81, First Round Proper |
| 22.11.1980 | | Gillingham | | Dagenham | | 2:1 |
| |
FA Cup 1977/78, First Round Proper |
| 30.11.1977 | | Weymouth | | Gillingham | | 0:1 * |
| |
FA Cup 1975/76, First Round Proper |
| 22.11.1975 | | Weymouth | | Gillingham | | 0:2 |
| |
FA Cup 1971/72, Second Round Proper |
| 11.12.1971 | | Romford | | Gillingham | | 0:1 |
| |
FA Cup 1971/72, First Round Proper |
| 20.11.1971 | | Gillingham | | Plymouth Argyle | | 3:2 |
| |
FA Cup 1969/70, Fourth Round Proper |
| 24.01.1970 | | Gillingham | | Peterborough United | | 5:1 (2:1) |
| |
FA Cup 1969/70, Third Round Proper |
| 03.01.1970 | | Gillingham | | Newport County | | 1:0 (0:0) |
| |
FA Cup 1969/70, Second Round Proper |
| 06.12.1969 | | Gillingham | | Tamworth | | 6:0 (4:0) |
| |
FA Cup 1969/70, First Round Proper |
| 19.11.1969 | | Gillingham | | Southend United | | 2:1 (2:0) * |
| |
FA Cup 1968/69, First Round Proper |
| 20.11.1968 | | Gillingham | | Orient | | 2:1 * |
| |
FA Cup 1966/67, First Round Proper |
| 26.11.1966 | | Gillingham | | Tamworth | | 4:1 |
| |
FA Cup 1964/65, First Round Proper |
| 18.11.1964 | | Gillingham | | Guildford City | | 1:0 * |
| |
FA Cup 1962/63, Second Round Proper |
| 24.11.1962 | | Gillingham | | Bedford Town | | 3:0 |
| |
FA Cup 1962/63, First Round Proper |
| 03.11.1962 | | Andover | | Gillingham | | 0:1 |
| |
FA Cup 1960/61, Second Round Proper |
| 26.11.1960 | | Gillingham | | Southend United | | 3:2 |
| |
FA Cup 1960/61, First Round Proper |
| 05.11.1960 | | Ashford Town | | Gillingham | | 1:2 |
| |
FA Cup 1959/60, Second Round Proper |
| 09.12.1959 | | Torquay United | | Gillingham | | 1:2 * |
| |
FA Cup 1959/60, First Round Proper |
| 14.11.1959 | | Bedford Town | | Gillingham | | 0:4 |
| |
FA Cup 1957/58, Second Round Proper |
| 11.12.1957 | | Gillingham | | Millwall | | 6:1 * |
| |
FA Cup 1957/58, First Round Proper |
| 16.11.1957 | | Gillingham | | Gorleston | | 10:1 |
| |
FA Cup 1956/57, First Round Proper |
| 21.11.1956 | | Gillingham | | Yiewsley | | 2:0 * |
| |
FA Cup 1954/55, First Round Proper |
| 20.11.1954 | | Gillingham | | Newport County | | 2:0 |
| |
FA Cup 1952/53, First Round Proper |
| 26.11.1952 | | Gillingham | | Wellington Town | | 3:0 * |
| |
FA Cup 1951/52, First Round Proper |
| 24.11.1951 | | Crystal Palace | | Gillingham | | 0:1 |
| |
FA Cup 1950/51, First Round Proper |
| 25.11.1950 | | Linby Colliery | | Gillingham | | 1:4 |
| |
FA Cup 1949/50, First Round Proper |
| 26.11.1949 | | Hastings United | | Gillingham | | 1:3 |
| |
FA Cup 1949/50, Fourth Qualifying Round |
| | | Guildford City | | Gillingham | | 2:3 |
| |
FA Cup 1947/48, Second Round Proper |
| 20.12.1947 | | Gillingham | | Rochdale | | 3:0 * |
| |
FA Cup 1947/48, First Round Proper |
| 29.11.1947 | | Gillingham | | Leyton Orient | | 1:0 |
| |
FA Cup 1947/48, Fourth Qualifying Round |
| | | Gillingham | | Barnet | | 3:1 |
| |
FA Cup 1946/47, Second Round Proper |
| 14.12.1946 | | Bristol City | | Gillingham | | 1:2 |
| |
FA Cup 1946/47, First Round Proper |
| 30.11.1946 | | Gillingham | | Gravesend & Northfleet | | 4:1 |
| |
FA Cup 1946/47, Fourth Qualifying Round |
| | | Guildford City | | Gillingham | | 1:2 |
| |
FA Cup 1936/37, First Round Proper |
| 28.11.1936 | | Ryde Sports | | Gillingham | | 1:5 |
| |
FA Cup 1935/36, First Round Proper |
| 30.11.1935 | | Exeter City | | Gillingham | | 0:4 |
| |
FA Cup 1933/34, First Round Proper |
| 25.11.1933 | | Oxford City | | Gillingham | | 1:5 |
| |
FA Cup 1932/33, First Round Proper |
| 30.11.1932 | | Wycombe Wanderers | | Gillingham | | 2:4 * |
| |
FA Cup 1930/31, First Round Proper |
| 29.11.1930 | | Gillingham | | Guildford City | | 7:2 |
| |
FA Cup 1927/28, Second Round Proper |
| 10.12.1927 | | Gillingham | | Southend United | | 2:0 |
| |
FA Cup 1927/28, First Round Proper |
| 26.11.1927 | | Gillingham | | Plymouth Argyle | | 2:1 |
| |
FA Cup 1926/27, First Round Proper |
| 01.12.1926 | | Gillingham | | Barking | | 2:0 * |
| |
FA Cup 1925/26, First Round Proper |
| 28.11.1925 | | Gillingham | | Southall | | 6:0 |
| |
FA Cup 1913/14, First Round Proper |
| 10.01.1914 | | Gillingham | | Blackpool | | 1:0 |
| |
FA Cup 1907/08, First Round Proper |
| 11.01.1908 | | New Brompton | | Sunderland | | 3:1 |
| |
FA Cup 1906/07, First Round Proper |
| 21.01.1907 | | New Brompton | | Burton United | | 2:0 * |
| |
FA Cup 1905/06, First Round Proper |
| 13.01.1906 | | New Brompton | | Northampton Town | | 2:1 |
| |