| Season | Competition |
Round Reached | Date |
Home | |
Away |
|
| 2007/2008 | F.A. Cup | 1st Round | Sat 10 Nov | Barnet | 2 - 1 | Gillingham |
| League Cup | 1st Round | Tue 14 Aug | Watford | 3 - 0 | Gillingham |
| (Associate Members) | Southern Section Semi-Final | Tue 08 Jan | Gillingham | 1 - 1 | Milton Keynes |
| Milton Keynes Dons won 5-4 on penalties |
|
| 2006/2007 | F.A. Cup | 2nd Round | Sun 03 Dec | Bristol City | 4 - 3 | Gillingham |
| League Cup | 1st Round | Tue 22 Aug | Millwall | 2 - 1 | Gillingham |
| (Associate Members) | Southern Section 1st Round | Tue 17 Oct | Gillingham | 1 - 2 | Nottm. Forest |
|
| 2005/2006 | F.A. Cup | 1st Round | Sat 05 Nov | Burscough | 3 - 2 | Gillingham |
| League Cup | 3rd Round | Tue 25 Oct | Doncaster Rvs. | 2 - 0 | Gillingham |
| (Associate Members) | Southern Section 2nd Round | Tue 22 Nov | Gillingham | 2 - 2 | Wycombe Wdrs. |
| after extra time, 90 minutes 2-2, Wycombe Wanderers won 3-1 on penalties |
|
| 2004/2005 | F.A. Cup | 3rd Round | Sat 08 Jan | Portsmouth | 1 - 0 | Gillingham |
| League Cup | 1st Round | Tue 24 Aug | Gillingham | 1 - 2 | Northampton |
|
| 2003/2004 | F.A. Cup | 4th Round | Sat 24 Jan | Burnley | 3 - 1 | Gillingham |
| League Cup | 3rd Round | Tue 28 Oct | Bolton Wdrs. | 2 - 0 | Gillingham |
|
| 2002/2003 | F.A. Cup | 4th Round Replay | Tue 04 Feb | Leeds Utd. | 2 - 1 | Gillingham |
| League Cup | 3rd Round | Wed 06 Nov | Chelsea | 2 - 1 | Gillingham |
|
| 2001/2002 | F.A. Cup | 5th Round | Sat 16 Feb | Arsenal | 5 - 2 | Gillingham |
| League Cup | 3rd Round | Tue 09 Oct | Gillingham | 0 - 2 | Southampton |
|
| 2000/2001 | F.A. Cup | 4th Round | Sun 28 Jan | Gillingham | 2 - 4 | Chelsea |
| League Cup | 2nd Round | Tue 26 Sep | Gillingham | 2 - 4 | Man. City |
|
| 1999/2000 | F.A. Cup | 6th Round | Sun 20 Feb | Chelsea | 5 - 0 | Gillingham |
| League Cup | 2nd Round | Tue 21 Sep | Bolton Wdrs. | 2 - 0 | Gillingham |
| Bolton Wanderers won 6-1 on aggregate |
| (Associate Members) | Southern Section 1st Round | Tue 07 Dec | Gillingham | 0 - 3 | Torquay Utd. |
|
| 1998/1999 | F.A. Cup | 1st Round | Sat 14 Nov | Oldham Ath. | 2 - 0 | Gillingham |
| League Cup | 1st Round | Tue 18 Aug | Gillingham | 0 - 1 | Southend Utd. |
| Southend United won 2-0 on aggregate |
| (Associate Members) | Southern Section Semi-Final | Tue 16 Feb | Millwall | 1 - 0 | Gillingham |
| after extra time, 90 minutes 0-0, Millwall won on golden goal rule |
|
| 1997/1998 | F.A. Cup | 1st Round Replay | Tue 25 Nov | Gillingham | 0 - 2 | Bristol Rvs. |
| League Cup | 1st Round | Tue 26 Aug | Birmingham C. | 3 - 0 | Gillingham |
| Birmingham City won 4-0 on aggregate |
| (Associate Members) | Southern Section 1st Round | Tue 09 Dec | Gillingham | 0 - 1 | Peterborough |
|
| 1996/1997 | F.A. Cup | 3rd Round | Tue 21 Jan | Gillingham | 0 - 2 | Derby County |
| League Cup | 4th Round | Tue 26 Nov | Ipswich Town | 1 - 0 | Gillingham |
| (Associate Members) | Southern Section 1st Round | Tue 10 Dec | Gillingham | 1 - 2 | Cardiff City |
| after extra time, 90 minutes 1-1, Cardiff won on the golden goal rule |
|
| 1995/1996 | F.A. Cup | 3rd Round | Sat 06 Jan | Reading | 3 - 1 | Gillingham |
| League Cup | 1st Round | Wed 23 Aug | Bristol Rvs. | 4 - 2 | Gillingham |
| Bristol Rovers won 5-3 on aggregate |
| (Associate Members) | Southern Section Preliminary Round Group Two | Tue 07 Nov | Gillingham | 2 - 2 | Hereford Utd. |
|
| 1994/1995 | F.A. Cup | 3rd Round | Sat 07 Jan | Gillingham | 1 - 2 | Sheff. Wed. |
| League Cup | 1st Round | Tue 23 Aug | Reading | 3 - 0 | Gillingham |
| Reading won 4-0 on aggregate |
| (Associate Members) | Southern Section 1st Round | Tue 29 Nov | Birmingham C. | 3 - 0 | Gillingham |
|
| 1993/1994 | F.A. Cup | 2nd Round | Sat 04 Dec | Plymouth Arg. | 2 - 0 | Gillingham |
| League Cup | 1st Round | Wed 25 Aug | Brighton & HA | 2 - 0 | Gillingham |
| Brighton & Hove Albion won 2-1 on aggregate |
| (Associate Members) | Southern Section Preliminary Round Group Two | Tue 09 Nov | Cambridge U. | 2 - 0 | Gillingham |
|
| 1992/1993 | F.A. Cup | 3rd Round Replay | Wed 13 Jan | Huddersfield | 2 - 1 | Gillingham |
| League Cup | 2nd Round | Wed 07 Oct | Southampton | 3 - 0 | Gillingham |
| Southampton won 3-0 on aggregate |
| (Associate Members) | Southern Section Preliminary Round Group Two | Tue 08 Dec | Gillingham | 3 - 3 | Fulham |
|
| 1991/1992 | F.A. Cup | 1st Round Replay | Tue 26 Nov | Gillingham | 1 - 3 | Brentford |
| League Cup | 1st Round | Tue 27 Aug | Gillingham | 3 - 4 | Portsmouth |
| Portsmouth won 6-4 on aggregate |
| (Associate Members) | Southern Section 1st Round | Tue 14 Jan | Fulham | 2 - 0 | Gillingham |
|
| 1990/1991 | F.A. Cup | 1st Round | Sat 17 Nov | Bournemouth | 2 - 1 | Gillingham |
| League Cup | 1st Round | Tue 04 Sep | Shrewsbury Tn. | 2 - 0 | Gillingham |
| Shrewsbury Town 2-1 on aggregate |
| (Associate Members) | Southern Section 1st Round | Tue 08 Jan | Gillingham | 0 - 1 | Hereford Utd. |
|
| 1989/1990 | F.A. Cup | 1st Round Replay | Wed 22 Nov | Welling Utd. | 1 - 0 | Gillingham |
| League Cup | 1st Round | Tue 29 Aug | Leyton Orient | 3 - 0 | Gillingham |
| Leyton Orient won 7-1 on aggregate |
| (Associate Members) | Southern Section 1st Round | Wed 24 Jan | Bristol Rvs. | 1 - 0 | Gillingham |
|
| 1988/1989 | F.A. Cup | 1st Round Replay | Wed 23 Nov | Peterborough | 1 - 0 | Gillingham |
| after extra time, 90 minutes 0-0 |
| League Cup | 2nd Round | Tue 11 Oct | Gillingham | 1 - 3 | Millwall |
| Millwall won 6-1 on aggregate |
| (Associate Members) | Southern Section 1st Round | Tue 17 Jan | Torquay Utd. | 3 - 0 | Gillingham |
|
| 1987/1988 | F.A. Cup | 3rd Round | Sat 09 Jan | Gillingham | 0 - 3 | Birmingham C. |
| League Cup | 2nd Round | Tue 06 Oct | Gillingham | 0 - 1 | Stoke City |
| Stoke City won 3-0 on aggregate |
| (Associate Members) | Southern Section Preliminary Round Group Three | Tue 27 Oct | Gillingham | 2 - 2 | Leyton Orient |
|
| 1986/1987 | F.A. Cup | 3rd Round | Mon 19 Jan | Wigan Ath. | 2 - 1 | Gillingham |
| League Cup | 2nd Round | Tue 07 Oct | Gillingham | 1 - 1 | Oxford Utd. |
| Oxford United won 7-1 on aggregate |
| (Associate Members) | Southern Section Semi-Final | Tue 10 Mar | Bristol City | 2 - 0 | Gillingham |
|
| 1985/1986 | F.A. Cup | 3rd Round Replay | Mon 13 Jan | Derby County | 3 - 1 | Gillingham |
| after extra time, 90 minutes ?-? |
| League Cup | 2nd Round | Tue 08 Oct | Portsmouth | 2 - 1 | Gillingham |
| Portsmouth won 5-2 on aggregate |
| (Associate Members) | Southern Section Semi-Final | Wed 16 Apr | Bristol City | 3 - 0 | Gillingham |
|
| 1984/1985 | F.A. Cup | 4th Round | Sat 26 Jan | Ipswich Town | 3 - 2 | Gillingham |
| League Cup | 2nd Round | Wed 10 Oct | Leeds Utd. | 3 - 2 | Gillingham |
| Leeds United won 5-3 on aggregate |
| (Associate Members) | Southern Section 1st Round | Tue 05 Feb | Colchester U. | 2 - 0 | Gillingham |
| Colchester United won 4-2 on aggregate |
|
| 1983/1984 | F.A. Cup | 4th Round 2nd Replay | Mon 06 Feb | Gillingham | 0 - 3 | Everton |
| League Cup | 1st Round | Tue 13 Sep | Chelsea | 4 - 0 | Gillingham |
| Chelsea won 6-1 on aggregate |
| (Associate Members) | Southern Section 1st Round | Tue 28 Feb | Millwall | 4 - 3 | Gillingham |
| after extra-time, 90 minutes 3-3 |
|
| 1982/1983 | F.A. Cup | 2nd Round Replay | Tue 14 Dec | Northampton | 3 - 2 | Gillingham |
| League Cup | 3rd Round | Tue 09 Nov | Gillingham | 2 - 4 | Tottenham H. |
|
| 1981/1982 | F.A. Cup | 4th Round | Sat 23 Jan | Gillingham | 0 - 1 | West Brom. |
| League Cup | 1st Round | Tue 15 Sep | Gillingham | 1 - 1 | Colchester U. |
| Colchester United won 3-1 on aggregate |
|
| 1980/1981 | F.A. Cup | 2nd Round 2nd Replay | Mon 22 Dec | Gillingham | 0 - 2 | Maidstone Utd. |
| League Cup | 2nd Round | Tue 02 Sep | Gillingham | 1 - 2 | Blackburn R. |
| Blackburn Rovers won 2-1 on aggregate |
|
| 1979/1980 | F.A. Cup | 1st Round Replay | Tue 27 Nov | Wimbledon | 4 - 2 | Gillingham |
| League Cup | 2nd Round | Wed 05 Sep | Norwich City | 4 - 2 | Gillingham |
| Norwich City won 5-3 on aggregate |
|
| 1978/1979 | F.A. Cup | 1st Round Replay | Tue 28 Nov | Gillingham | 1 - 2 | Reading |
| after extra time, 90 minutes ?-? |
| League Cup | 1st Round | Tue 15 Aug | Gillingham | 1 - 2 | Reading |
| Reading won 5-2 on aggregate |
|
| 1977/1978 | F.A. Cup | 2nd Round Replay | Tue 20 Dec | Peterborough | 2 - 0 | Gillingham |
| League Cup | 1st Round | Tue 16 Aug | Wimbledon | 3 - 1 | Gillingham |
| Wimbledon won 4-2 on aggregate |
|
| 1976/1977 | F.A. Cup | 1st Round | Sat 20 Nov | Gillingham | 0 - 1 | Watford |
| League Cup | 2nd Round | Wed 01 Sep | Gillingham | 1 - 2 | Newcastle Utd. |
|
| 1975/1976 | F.A. Cup | 2nd Round | Sat 13 Dec | Gillingham | 0 - 1 | Brighton & HA |
| League Cup | 2nd Round | Tue 09 Sep | Carlisle Utd. | 2 - 0 | Gillingham |
|
| 1974/1975 | F.A. Cup | 1st Round | Tue 26 Nov | Hereford Utd. | 1 - 0 | Gillingham |
| League Cup | 1st Round 2nd Replay | Tue 03 Sep | Bournemouth | 2 - 1 | Gillingham |
|
| 1973/1974 | F.A. Cup | 1st Round | Sat 24 Nov | Cambridge U. | 3 - 2 | Gillingham |
| League Cup | 2nd Round | Wed 10 Oct | Gillingham | 1 - 2 | Carlisle Utd. |
|
| 1972/1973 | F.A. Cup | 1st Round | Sat 18 Nov | Gillingham | 1 - 2 | Reading |
| League Cup | 2nd Round | Tue 05 Sep | Gillingham | 0 - 2 | Millwall |
|
| 1971/1972 | F.A. Cup | 3rd Round | Sat 15 Jan | Swansea City | 1 - 0 | Gillingham |
| League Cup | 3rd Round Replay | Tue 12 Oct | Grimsby Town | 1 - 0 | Gillingham |
|
| 1970/1971 | F.A. Cup | 1st Round | Sat 21 Nov | Brentford | 2 - 1 | Gillingham |
| League Cup | 1st Round | Wed 19 Aug | Gillingham | 0 - 1 | Luton Town |
|
| 1969/1970 | F.A. Cup | 5th Round | Sat 07 Feb | Watford | 2 - 1 | Gillingham |
| League Cup | 2nd Round | Wed 03 Sep | Blackpool | 3 - 1 | Gillingham |
|
| 1968/1969 | F.A. Cup | 2nd Round | Sat 07 Dec | Luton Town | 3 - 1 | Gillingham |
| League Cup | 1st Round Replay | Tue 20 Aug | Orient | 3 - 0 | Gillingham |
|
| 1967/1968 | F.A. Cup | 1st Round | Mon 18 Dec | Newport Co. | 3 - 0 | Gillingham |
| League Cup | 2nd Round Replay | Wed 20 Sep | Torquay Utd. | 2 - 0 | Gillingham |
|
| 1966/1967 | F.A. Cup | 2nd Round | Sat 07 Jan | Walsall | 3 - 1 | Gillingham |
| League Cup | 2nd Round 2nd Replay | Wed 28 Sep | Arsenal | 5 - 0 | Gillingham |
|
| 1965/1966 | F.A. Cup | 1st Round | Sat 13 Nov | Gillingham | 1 - 2 | Folkestone |
| League Cup | 2nd Round | Wed 22 Sep | Blackpool | 5 - 2 | Gillingham |
|
| 1964/1965 | F.A. Cup | 2nd Round | Sat 05 Dec | Luton Town | 1 - 0 | Gillingham |
| League Cup | 1st Round | Wed 02 Sep | Exeter City | 2 - 0 | Gillingham |
|
| 1963/1964 | F.A. Cup | 1st Round | Sat 16 Nov | Q.P.R. | 4 - 1 | Gillingham |
| League Cup | 4th Round | Wed 27 Nov | Leicester City | 4 - 1 | Gillingham |
|
| 1962/1963 | F.A. Cup | 3rd Round | Wed 27 Feb | Gillingham | 2 - 4 | Port Vale |
| League Cup | 1st Round | Wed 05 Sep | Newport Co. | 2 - 1 | Gillingham |
|
| 1961/1962 | F.A. Cup | 1st Round | Sat 04 Nov | Coventry City | 2 - 0 | Gillingham |
| League Cup | 1st Round | Mon 11 Sep | Nottm. Forest | 4 - 1 | Gillingham |
|
| 1960/1961 | F.A. Cup | 3rd Round | Sat 07 Jan | Gillingham | 2 - 6 | Leyton Orient |
| League Cup | 2nd Round Replay | Tue 25 Oct | Preston N.E. | 3 - 0 | Gillingham |
|
| 1959/1960 | F.A. Cup | 3rd Round | Sat 09 Jan | Gillingham | 1 - 4 | Swansea Town |
|
| 1958/1959 | F.A. Cup | 1st Round Replay | Wed 19 Nov | Gillingham | 1 - 4 | Plymouth Arg. |
|
| 1957/1958 | F.A. Cup | 3rd Round | Sat 04 Jan | Nottm. Forest | 2 - 0 | Gillingham |
|
| 1956/1957 | F.A. Cup | 2nd Round | Sat 08 Dec | Gillingham | 1 - 2 | Newport Co. |
|
| 1955/1956 | F.A. Cup | 1st Round Replay | Thu 24 Nov | Shrewsbury Tn. | 4 - 1 | Gillingham |
| after extra time, 90 minutes ?-? |
|
| 1954/1955 | F.A. Cup | 2nd Round Replay | Mon 13 Dec | Reading | 5 - 3 | Gillingham |
|
| 1953/1954 | F.A. Cup | 1st Round | Sat 21 Nov | Walthamstow Av | 1 - 0 | Gillingham |
|
| 1952/1953 | F.A. Cup | 2nd Round | Sat 06 Dec | Stockport Co. | 3 - 1 | Gillingham |
|
| 1951/1952 | F.A. Cup | 2nd Round | Sat 15 Dec | Gillingham | 0 - 3 | Rochdale |
|
| 1950/1951 | F.A. Cup | 2nd Round 2nd Replay | Mon 18 Dec | Bristol Rvs. | 2 - 1 | Gillingham |
| played at neutral ground |
|
| 1949/1950 | F.A. Cup | 2nd Round | Sat 10 Dec | Yeovil Town | 3 - 1 | Gillingham |
|
| 1947/1948 | F.A. Cup | 3rd Round Replay | Sat 17 Jan | Q.P.R. | 3 - 1 | Gillingham |
|
| 1946/1947 | F.A. Cup | 3rd Round | Sat 11 Jan | Swansea Town | 4 - 1 | Gillingham |
|
| 1937/1938 | F.A. Cup | 1st Round | Sat 27 Nov | Gillingham | 3 - 4 | Swindon Town |
|
| 1936/1937 | F.A. Cup | 2nd Round | Sat 12 Dec | Wrexham | 2 - 0 | Gillingham |
|
| 1935/1936 | F.A. Cup | 2nd Round | Sat 14 Dec | Crewe Alex. | 2 - 1 | Gillingham |
|
| 1934/1935 | F.A. Cup | 1st Round | Sat 24 Nov | Bristol City | 2 - 0 | Gillingham |
|
| 1933/1934 | F.A. Cup | 2nd Round | Sat 09 Dec | Charlton Ath. | 1 - 0 | Gillingham |
|
| 1932/1933 | F.A. Cup | 2nd Round Replay | Wed 14 Dec | Gillingham | 1 - 3 | Bristol Rvs. |
|
| 1931/1932 | F.A. Cup | 1st Round | Sat 28 Nov | Bristol Rvs. | 5 - 1 | Gillingham |
|
| 1930/1931 | F.A. Cup | 2nd Round | Sat 13 Dec | Gillingham | 1 - 3 | Aldershot |
|
| 1929/1930 | F.A. Cup | 1st Round | Sat 30 Nov | Gillingham | 0 - 2 | Margate |
|
| 1928/1929 | F.A. Cup | 1st Round Replay | Wed 28 Nov | Torquay Utd. | 5 - 1 | Gillingham |
|
| 1927/1928 | F.A. Cup | 3rd Round | Sat 14 Jan | Stoke City | 6 - 1 | Gillingham |
|
| 1926/1927 | F.A. Cup | 2nd Round Replay | Wed 15 Dec | Brentford | 1 - 0 | Gillingham |
|
| 1925/1926 | F.A. Cup | 2nd Round | Sat 12 Dec | Southend Utd. | 1 - 0 | Gillingham |
|
| 1923/1924 | F.A. Cup | 1st Round Replay | Wed 16 Jan | Gillingham | 0 - 2 | Cardiff City |
|
| 1921/1922 | F.A. Cup | 1st Round | Sat 07 Jan | Gillingham | 1 - 3 | Oldham Ath. |
|
| 1919/1920 | F.A. Cup | 1st Round | Sat 17 Jan | West Stanley | 3 - 1 | Gillingham |
|
| 1914/1915 | F.A. Cup | 1st Round | Sat 09 Jan | Rochdale | 2 - 0 | Gillingham |
|
| 1913/1914 | F.A. Cup | 2nd Round | Sat 31 Jan | Liverpool | 2 - 0 | Gillingham |
|
| 1912/1913 | F.A. Cup | 1st Round Replay | Thu 16 Jan | Barnsley | 3 - 1 | Gillingham |
>> LIVE SCORES
