FA Cup 2022/23, Second Round Proper |
 | 26.11.2022 |  | Dagenham & Redbridge | – | Gillingham | | 1:1 (0:0) |
| London |
FA Cup 2022/23, First Round Proper |
| 05.11.2022 | | AFC Fylde | – | Gillingham | | 1:1 (0:1) |
| Wesham |
FA Cup 2021/22, First Round Proper |
| 06.11.2021 | | Gillingham | – | Cheltenham Town | | 1:1 (0:1) |
| Gillingham |
FA Cup 2019/20, First Round Proper |
| 09.11.2019 | | Sunderland | – | Gillingham | | 1:1 (1:0) |
| Sunderland |
FA Cup 2018/19, First Round Proper |
| 10.11.2018 | | Gillingham | – | Hartlepool United | | 0:0 |
| Gillingham |
FA Cup 2017/18, Second Round Proper |
| 02.12.2017 | | Gillingham | – | Carlisle United | | 1:1 (1:1) |
| Gillingham |
FA Cup 2016/17, First Round Proper |
| 05.11.2016 | | Gillingham | – | Brackley Town | | 2:2 (2:2) |
| Gillingham |
FA Cup 2013/14, First Round Proper |
| 09.11.2013 | | Gillingham | – | Brackley Town | | 1:1 (0:0) |
| Gillingham |
FA Cup 2011/12, First Round Proper |
| 12.11.2011 | | A.F.C. Bournemouth | – | Gillingham | | 3:3 (1:1) |
| Bournemouth |
FA Cup 2008/09, Second Round Proper |
| 29.11.2008 | | Gillingham | – | Stockport County | | 0:0 |
| Gillingham |
FA Cup 2002/03, Fourth Round Proper |
| 25.01.2003 | | Gillingham | – | Leeds United | | 1:1 (0:0) |
| Gillingham |
FA Cup 1999/00, Third Round Proper |
| 11.12.1999 | | Walsall | – | Gillingham | | 1:1 (0:1) |
| Walsall |
FA Cup 1999/00, First Round Proper |
| 30.10.1999 | | Cheltenham Town | – | Gillingham | | 1:1 (0:1) |
| Cheltenham |
FA Cup 1997/98, First Round Proper |
| 14.11.1997 | | Bristol Rovers | – | Gillingham | | 2:2 (1:1) |
| Bristol |
FA Cup 1995/96, First Round Proper |
| 13.11.1995 | | Wycombe Wanderers | – | Gillingham | | 1:1 (0:0) |
| High Wycombe |
FA Cup 1994/95, Second Round Proper |
| 03.12.1994 | | Gillingham | – | Fulham | | 1:1 (1:0) |
| Gillingham |
FA Cup 1993/94, First Round Proper |
| 13.11.1993 | | Yeading | – | Gillingham | | 0:0 |
| London |
FA Cup 1992/93, Third Round Proper |
| 02.01.1993 | | Gillingham | – | Huddersfield Town | | 0:0 |
| Gillingham |
FA Cup 1992/93, Second Round Proper |
| 05.12.1992 | | Gillingham | – | Colchester United | | 1:1 (1:0) |
| Gillingham |
FA Cup 1991/92, First Round Proper |
| 18.11.1991 | | Brentford | – | Gillingham | | 3:3 |
| Brentford |
FA Cup 1989/90, First Round Proper |
| 18.11.1989 | | Gillingham | – | Welling United | | 0:0 |
| Gillingham |
FA Cup 1988/89, First Round Proper |
| 19.11.1988 | | Gillingham | – | Peterborough United | | 3:3 (0:1) |
| Gillingham |
FA Cup 1985/86, Third Round Proper |
| 04.01.1986 | | Gillingham | – | Derby County | | 1:1 |
| |
FA Cup 1983/84, Fourth Round Proper |
| 31.01.1984 | | Gillingham | – | Everton | | 0:0 aet * |
| |
FA Cup 1983/84, Fourth Round Proper |
| 28.01.1984 | | Everton | – | Gillingham | | 0:0 |
| Liverpool |
FA Cup 1982/83, Second Round Proper |
| 11.12.1982 | | Gillingham | – | Northampton Town | | 1:1 |
| |
FA Cup 1981/82, Second Round Proper |
| 15.12.1981 | | Gillingham | – | Barking | | 1:1 |
| |
FA Cup 1981/82, First Round Proper |
| 21.11.1981 | | Plymouth Argyle | – | Gillingham | | 0:0 |
| |
FA Cup 1980/81, Second Round Proper |
| 16.12.1980 | | Maidstone United | – | Gillingham | | 0:0 aet * |
| |
FA Cup 1980/81, Second Round Proper |
| 13.12.1980 | | Gillingham | – | Maidstone United | | 0:0 |
| |
FA Cup 1979/80, First Round Proper |
| 24.11.1979 | | Gillingham | – | Wimbledon | | 0:0 |
| |
FA Cup 1978/79, First Round Proper |
| 25.11.1978 | | Reading | – | Gillingham | | 0:0 |
| |
FA Cup 1977/78, Second Round Proper |
| 17.12.1977 | | Gillingham | – | Peterborough United | | 1:1 |
| |
FA Cup 1977/78, First Round Proper |
| 26.11.1977 | | Gillingham | – | Weymouth | | 1:1 |
| |
FA Cup 1969/70, First Round Proper |
| 15.11.1969 | | Southend United | – | Gillingham | | 0:0 |
| |
FA Cup 1968/69, First Round Proper |
| 16.11.1968 | | Orient | – | Gillingham | | 1:1 |
| |
FA Cup 1964/65, First Round Proper |
| 14.11.1964 | | Guildford City | – | Gillingham | | 2:2 |
| |
FA Cup 1959/60, Second Round Proper |
| 05.12.1959 | | Gillingham | – | Torquay United | | 2:2 |
| |
FA Cup 1958/59, First Round Proper |
| 15.11.1958 | | Plymouth Argyle | – | Gillingham | | 2:2 |
| |
FA Cup 1957/58, Second Round Proper |
| 07.12.1957 | | Millwall | – | Gillingham | | 1:1 |
| |
FA Cup 1956/57, First Round Proper |
| 17.11.1956 | | Yiewsley | – | Gillingham | | 2:2 |
| |
FA Cup 1955/56, First Round Proper |
| 19.11.1955 | | Gillingham | – | Shrewsbury Town | | 1:1 |
| |
FA Cup 1954/55, Second Round Proper |
| 11.12.1954 | | Gillingham | – | Reading | | 1:1 |
| |
FA Cup 1952/53, First Round Proper |
| 22.11.1952 | | Wellington Town | – | Gillingham | | 1:1 |
| |
FA Cup 1950/51, Second Round Proper |
| 13.12.1950 | | Gillingham | – | Bristol Rovers | | 1:1 aet * |
| |
FA Cup 1950/51, Second Round Proper |
| 09.12.1950 | | Bristol Rovers | – | Gillingham | | 2:2 |
| |
FA Cup 1947/48, Third Round Proper |
| 10.01.1948 | | Gillingham | – | Queens Park Rangers | | 1:1 |
| |
FA Cup 1947/48, Second Round Proper |
| 13.12.1947 | | Rochdale | – | Gillingham | | 1:1 |
| |
FA Cup 1932/33, Second Round Proper |
| 10.12.1932 | | Bristol Rovers | – | Gillingham | | 1:1 |
| |
FA Cup 1932/33, First Round Proper |
| 26.11.1932 | | Gillingham | – | Wycombe Wanderers | | 1:1 |
| |
FA Cup 1928/29, First Round Proper |
| 24.11.1928 | | Gillingham | – | Torquay United | | 0:0 |
| |
FA Cup 1926/27, Second Round Proper |
| 11.12.1926 | | Gillingham | – | Brentford | | 1:1 |
| |
FA Cup 1926/27, First Round Proper |
| 27.11.1926 | | Barking | – | Gillingham | | 0:0 |
| |
FA Cup 1923/24, First Round Proper |
| 12.01.1924 |  | Cardiff City | – | Gillingham | | 0:0 |
| |
FA Cup 1912/13, First Round Proper |
| 11.01.1913 | | Gillingham | – | Barnsley | | 0:0 |
| |
FA Cup 1909/10, First Round Proper |
| 19.01.1910 | | New Brompton | – | Leyton | | 2:2 aet * |
| |
FA Cup 1909/10, First Round Proper |
| 15.01.1910 | | Leyton | – | New Brompton | | 0:0 |
| |
FA Cup 1907/08, Second Round Proper |
| 01.02.1908 | | Manchester City | – | New Brompton | | 1:1 |
| |
FA Cup 1906/07, First Round Proper |
| 16.01.1907 | | New Brompton | – | Burton United | | 0:0 aet * |
| |
FA Cup 1906/07, First Round Proper |
| 12.01.1907 | | Burton United | – | New Brompton | | 0:0 |
| |
FA Cup 1905/06, Second Round Proper |
| 03.02.1906 | | New Brompton | – | Southampton | | 0:0 |
| |
FA Cup 1903/04, Intermediate Round |
| 12.12.1903 | | New Brompton | – | Bristol City | | 1:1 |
| |
