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| Year | Round | Home | Away | P | W | D | L | GF | GA | Win | Draw | Loss | Gills Gls | Away Gls | |
| 291 | 118 | 71 | 102 | 493 | 410 | ||||||||||
| 2005/2006 | FA Cup 1st Rd | Burscough | 3-2 | Gillingham | 0 | 0 | 1 | 2 | 3 | ||||||
| 2004/2005 | FA Cup 3rd Rd | Portsmouth | 1-0 | Gillingham | 0 | 0 | 1 | 0 | 1 | ||||||
| 2003/2004 | FA Cup 4th Rd | Burnley | 3-1 | Gillingham | 0 | 0 | 1 | 1 | 3 | ||||||
| FA Cup 3rd Rd | Gillingham | 3-2 | Charlton Athletic | 1 | 0 | 0 | 3 | 2 | |||||||
| 2002/2003 | FA Cup 4th Rd Replay | Leeds United | 2-1 | Gillingham | 0 | 0 | 1 | 1 | 2 | ||||||
| FA Cup 4th Rd | Gillingham | 1-1 | Leeds United | 0 | 1 | 0 | 1 | 1 | |||||||
| FA Cup 3rd Rd | Gillingham | 4-1 | Sheffield Wednesday | 1 | 0 | 0 | 4 | 1 | |||||||
| 2001/2002 | FA Cup 5th Rd | Arsenal | 5-2 | Gillingham | 0 | 0 | 1 | 2 | 5 | ||||||
| FA Cup 4th Rd | Gillingham | 1-0 | Bristol Rovers | 1 | 0 | 0 | 1 | 0 | |||||||
| FA Cup 3rd Rd | Wolverhampton Wanderers | 0-1 | Gillingham | 1 | 0 | 0 | 1 | 0 | |||||||
| 2000/2001 | FA Cup 4th Rd | Gillingham | 2-4 | Chelsea | 0 | 0 | 1 | 2 | 4 | ||||||
| FA Cup 3rd Rd | Bournemouth | 2-3 | Gillingham | 1 | 0 | 0 | 3 | 2 | |||||||
| 1999/2000 | FA Cup 6th Rd | Chelsea | 5-0 | Gillingham | 0 | 0 | 1 | 0 | 5 | ||||||
| FA Cup 5th Rd | Gillingham | 3-1 | Sheffield Wednesday | 1 | 0 | 0 | 3 | 1 | |||||||
| FA Cup 4th Rd | Gillingham | 3-1 | Bradford City | 1 | 0 | 0 | 3 | 1 | |||||||
| FA Cup 3rd Rd Replay | Gillingham | 2-1 | Walsall | 1 | 0 | 0 | 2 | 1 | |||||||
| FA Cup 3rd Rd | Walsall | 1-1 | Gillingham | 0 | 1 | 0 | 1 | 1 | |||||||
| FA Cup 2nd Rd | Gillingham | 3-1 | Darlington | 1 | 0 | 0 | 3 | 1 | |||||||
| FA Cup 1st Rd Replay | Gillingham | 3-2 | Cheltenham Town | 1 | 0 | 0 | 3 | 2 | |||||||
| FA Cup 1st Rd | Cheltenham Town | 1-1 | Gillingham | 0 | 1 | 0 | 1 | 1 | |||||||
| 1998/1999 | FA Cup 1st Rd | Oldham Athletic | 2-0 | Gillingham | 0 | 0 | 1 | 0 | 2 | ||||||
| 1997/1998 | FA Cup 1st Rd Replay | Gillingham | 0-2 | Bristol Rovers | 0 | 0 | 1 | 0 | 2 | ||||||
| FA Cup 1st Rd | Bristol Rovers | 2-2 | Gillingham | 0 | 1 | 0 | 2 | 2 | |||||||
| 1996/1997 | FA Cup 3rd Rd | Gillingham | 0-2 | Derby County | 0 | 0 | 1 | 0 | 2 | ||||||
| FA Cup 3rd Rd | Gillingham | abd | Derby County | ||||||||||||
| abandoned at 0-0 | |||||||||||||||
| FA Cup 2nd Rd | Cardiff City | 0-2 | Gillingham | 1 | 0 | 0 | 2 | 0 | |||||||
| FA Cup 1st Rd | Gillingham | 1-0 | Hereford United | 1 | 0 | 0 | 1 | 0 | |||||||
| 1995/1996 | FA Cup 3rd Rd | Reading | 3-1 | Gillingham | 0 | 0 | 1 | 1 | 3 | ||||||
| FA Cup 2nd Rd | Gillingham | 3-0 | Hitchin Town | 1 | 0 | 0 | 3 | 0 | |||||||
| FA Cup 1st Rd Replay | Gillingham | 1-0 | Wycombe Wanderers | 1 | 0 | 0 | 1 | 0 | |||||||
| FA Cup 1st Rd | Wycombe Wanderers | 1-1 | Gillingham | 0 | 1 | 0 | 1 | 1 | |||||||
| 1994/1995 | FA Cup 3rd Rd | Gillingham | 1-2 | Sheffield Wednesday | 0 | 0 | 1 | 1 | 2 | ||||||
| FA Cup 2nd Rd Replay | Fulham | 1-2 | Gillingham | 1 | 0 | 0 | 2 | 1 | |||||||
| FA Cup 2nd Rd | Gillingham | 1-1 | Fulham | 0 | 1 | 0 | 1 | 1 | |||||||
| FA Cup 1st Rd | Heybridge Swifts | 0-2 | Gillingham | 1 | 0 | 0 | 2 | 0 | |||||||
| at Colchester United | |||||||||||||||
| 1993/1994 | FA Cup 2nd Rd | Plymouth Argyle | 2-0 | Gillingham | 0 | 0 | 1 | 0 | 2 | ||||||
| FA Cup 1st Rd Replay | Gillingham | 3-1 | Yeading | 1 | 0 | 0 | 3 | 1 | |||||||
| FA Cup 1st Rd | Yeading | 0-0 | Gillingham | 0 | 1 | 0 | 0 | 0 | |||||||
| 1992/1993 | FA Cup 3rd Rd Replay | Huddersfield Town | 2-1 | Gillingham | 0 | 0 | 1 | 1 | 2 | ||||||
| FA Cup 3rd Rd | Gillingham | 0-0 | Huddersfield Town | 0 | 1 | 0 | 0 | 0 | |||||||
| FA Cup 2nd Rd Replay | Colchester United | 2-3 | Gillingham | 1 | 0 | 0 | 3 | 2 | |||||||
| FA Cup 2nd Rd | Gillingham | 1-1 | Colchester United | 0 | 1 | 0 | 1 | 1 | |||||||
| English FA Cup 1st Rd | Gillingham | 3-2 | Kettering Town | 1 | 0 | 0 | 3 | 2 | |||||||
| 1991/1992 | FA Cup 1st Rd | Gillingham | 1-3 | Brentford | 0 | 0 | 1 | 1 | 3 | ||||||
| 1990/1991 | FA Cup 1st Rd | Bournemouth | 2-1 | Gillingham | 0 | 0 | 1 | 1 | 2 | ||||||
| 1989/90 | English FA Cup 1st Rd Replay | Welling United | 3-1 | Gillingham | 0 | 0 | 1 | 1 | 3 | ||||||
| English FA Cup 1st Rd | Gillingham | 0-0 | Welling United | 0 | 1 | 0 | 0 | 0 | |||||||
| 1988/1989 | FA Cup 1st Rd Replay | Peterborough United | 1-0 | Gillingham | 0 | 0 | 1 | 0 | 1 | ||||||
| FA Cup 1st Rd | Gillingham | 3-3 | Peterborough United | 0 | 1 | 0 | 3 | 3 | |||||||
| 1987/1988 | FA Cup 3rd Rd | Gillingham | 0-3 | Birmingham City | 0 | 0 | 1 | 0 | 3 | ||||||
| FA Cup 2nd Rd | Gillingham | 2-1 | Walsall | 1 | 0 | 0 | 2 | 1 | |||||||
| FA Cup 1st Rd | Gillingham | 2-1 | Fulham | 1 | 0 | 0 | 2 | 1 | |||||||
| 1986/1987 | FA Cup 3rd Rd | Wigan Athletic | 2-1 | Gillingham | 0 | 0 | 1 | 1 | 2 | ||||||
| FA Cup 2nd Rd | Gillingham | 2-0 | Chelmsford City | 1 | 0 | 0 | 2 | 0 | |||||||
| FA Cup 1st Rd | Kettering Town | 0-3 | Gillingham | 1 | 0 | 0 | 3 | 0 | |||||||
| 1985/1986 | FA Cup 3rd Rd Replay | Derby County | 3-1 | Gillingham | 0 | 0 | 1 | 1 | 3 | ||||||
| FA Cup 3rd Rd | Gillingham | 1-1 | Derby County | 0 | 1 | 0 | 1 | 1 | |||||||
| FA Cup 2nd Rd | Gillingham | 6-1 | Bognor Regis Town | 1 | 0 | 0 | 6 | 1 | |||||||
| FA Cup 1st Rd | Gillingham | 3-0 | Northampton Town | 1 | 0 | 0 | 3 | 0 | |||||||
| 1984/1985 | FA Cup 4th Rd | Ipswich Town | 3-2 | Gillingham | 0 | 0 | 1 | 2 | 3 | ||||||
| FA Cup 3rd Rd | Gillingham | 2-1 | Cardiff City | 1 | 0 | 0 | 2 | 1 | |||||||
| FA Cup 2nd Rd | Colchester United | 0-5 | Gillingham | 1 | 0 | 0 | 5 | 0 | |||||||
| FA Cup 1st Rd | Gillingham | 2-1 | Windsor and Eton | 1 | 0 | 0 | 2 | 1 | |||||||
| 1983/1984 | FA Cup 4th Rd 2nd Replay | Gillingham | 0-3 | Everton | 0 | 0 | 1 | 0 | 3 | ||||||
| FA Cup 4th Rd Replay | Gillingham | 0-0 | Everton | 0 | 1 | 0 | 0 | 0 | |||||||
| FA Cup 4th Rd | Everton | 0-0 | Gillingham | 0 | 1 | 0 | 0 | 0 | |||||||
| FA Cup 3rd Rd | Gillingham | 5-3 | Brentford | 1 | 0 | 0 | 5 | 3 | |||||||
| FA Cup 2nd Rd | Gillingham | 6-1 | Chelmsford City | 1 | 0 | 0 | 6 | 1 | |||||||
| FA Cup 1st Rd | AP Leamington | 0-1 | Gillingham | 1 | 0 | 0 | 1 | 0 | |||||||
| 1982/1983 | FA Cup 2nd Rd Replay | Northampton Town | 3-2 | Gillingham | 0 | 0 | 1 | 2 | 3 | ||||||
| FA Cup 2nd Rd | Gillingham | 1-1 | Northampton Town | 0 | 1 | 0 | 1 | 1 | |||||||
| FA Cup 1st Rd | Gillingham | 1-0 | Dagenham | 1 | 0 | 0 | 1 | 0 | |||||||
| 1981/1982 | FA Cup 4th Rd | Gillingham | 0-1 | West Bromwich Albion | 0 | 0 | 1 | 0 | 1 | ||||||
| FA Cup 3rd Rd | Gillingham | 2-1 | Oldham Athletic | 1 | 0 | 0 | 2 | 1 | |||||||
| FA Cup 2nd Rd Replay | Gillingham | 3-1 | Barking | 1 | 0 | 0 | 3 | 1 | |||||||
| FA Cup 2nd Rd | Gillingham | 1-1 | Barking | 0 | 1 | 0 | 1 | 1 | |||||||
| FA Cup 1st Rd Replay | Gillingham | 1-0 | Plymouth Argyle | 1 | 0 | 0 | 1 | 0 | |||||||
| FA Cup 1st Rd | Plymouth Argyle | 0-0 | Gillingham | 0 | 1 | 0 | 0 | 0 | |||||||
| 1980/1981 | FA Cup 2nd Rd 2nd Replay | Gillingham | 0-2 | Maidstone United | 0 | 0 | 1 | 0 | 2 | ||||||
| FA Cup 2nd Rd Replay | Maidstone United | 0-0 | Gillingham | 0 | 1 | 0 | 0 | 0 | |||||||
| FA Cup 2nd Rd | Gillingham | 0-0 | Maidstone United | 0 | 1 | 0 | 0 | 0 | |||||||
| FA Cup 1st Rd | Gillingham | 2-1 | Dagenham | 1 | 0 | 0 | 2 | 1 | |||||||
| 1979/1980 | FA Cup 1st Rd Replay | Wimbledon | 4-2 | Gillingham | 0 | 0 | 1 | 2 | 4 | ||||||
| FA Cup 1st Rd | Gillingham | 0-0 | Wimbledon | 0 | 1 | 0 | 0 | 0 | |||||||
| 1978/1979 | FA Cup 1st Rd Replay | Gillingham | 1-2 | Reading | 0 | 0 | 1 | 1 | 2 | ||||||
| FA Cup 1st Rd | Reading | 0-0 | Gillingham | 0 | 1 | 0 | 0 | 0 | |||||||
| 1977/78 | FA Cup 2nd Rd Replay | Peterborough United | 2-0 | Gillingham | 0 | 0 | 1 | 0 | 2 | ||||||
| FA Cup 2nd Rd | Gillingham | 1-1 | Peterborough United | 0 | 1 | 0 | 1 | 1 | |||||||
| FA Cup 1st Rd Replay | Weymouth | 0-1 | Gillingham | 1 | 0 | 0 | 1 | 0 | |||||||
| FA Cup 1st Rd | Gillingham | 1-1 | Weymouth | 0 | 1 | 0 | 1 | 1 | |||||||
| 1976/1977 | FA Cup 1st Rd | Gillingham | 0-1 | Watford | 0 | 0 | 1 | 0 | 1 | ||||||
| 1975/1976 | FA Cup 2nd Rd | Gillingham | 0-1 | Brighton & Hove Albion | 0 | 0 | 1 | 0 | 1 | ||||||
| FA Cup 1st Rd | Weymouth | 0-2 | Gillingham | 1 | 0 | 0 | 2 | 0 | |||||||
| 1974/1975 | FA Cup 1st Rd | Hereford United | 1-0 | Gillingham | 0 | 0 | 1 | 0 | 1 | ||||||
| 1973/1974 | FA Cup 1st Rd | Cambridge United | 3-2 | Gillingham | 0 | 0 | 1 | 2 | 3 | ||||||
| 1972/1973 | FA Cup 1st Rd | Gillingham | 1-2 | Reading | 0 | 0 | 1 | 1 | 2 | ||||||
| 1971/1972 | FA Cup 3rd Rd | Swansea City | 1-0 | Gillingham | 0 | 0 | 1 | 0 | 1 | ||||||
| FA Cup 2nd Rd | Romford | 0-1 | Gillingham | 1 | 0 | 0 | 1 | 0 | |||||||
| FA Cup 1st Rd | Gillingham | 3-2 | Plymouth Argyle | 1 | 0 | 0 | 3 | 2 | |||||||
| 1970/1971 | FA Cup 1st Rd | Brentford | 2-1 | Gillingham | 0 | 0 | 1 | 1 | 2 | ||||||
| 1969/1970 | FA Cup 5th Rd | Watford | 2-1 | Gillingham | 0 | 0 | 1 | 1 | 2 | ||||||
| FA Cup 4th Rd | Gillingham | 5-1 | Peterborough United | 1 | 0 | 0 | 5 | 1 | |||||||
| FA Cup 3rd Rd | Gillingham | 1-0 | Newport County | 1 | 0 | 0 | 1 | 0 | |||||||
| FA Cup 2nd Rd | Gillingham | 6-0 | Tamworth | 1 | 0 | 0 | 6 | 0 | |||||||
| FA Cup 1st Rd Replay | Gillingham | 2-0 | Southend United | 1 | 0 | 0 | 2 | 0 | |||||||
| FA Cup 1st Rd | Southend United | 0-0 | Gillingham | 0 | 1 | 0 | 0 | 0 | |||||||
| 1968/1969 | FA Cup 2nd Rd | Luton Town | 3-1 | Gillingham | 0 | 0 | 1 | 1 | 3 | ||||||
| FA Cup 1st Rd Replay | Gillingham | 2-1 | Leyton Orient | 1 | 0 | 0 | 2 | 1 | |||||||
| FA Cup 1st Rd | Leyton Orient | 1-1 | Gillingham | 0 | 1 | 0 | 1 | 1 | |||||||
| 1967/1968 | FA Cup 1st Rd | Newport County | 3-0 | Gillingham | 0 | 0 | 1 | 0 | 3 | ||||||
| 1966/1967 | FA Cup 2nd Rd | Walsall | 3-1 | Gillingham | 0 | 0 | 1 | 1 | 3 | ||||||
| FA Cup 1st Rd | Gillingham | 4-1 | Tamworth | 1 | 0 | 0 | 4 | 1 | |||||||
| 1965/66 | FA Cup 1st Rd | Gillingham | 1-2 | Folkestone Town | 0 | 0 | 1 | 1 | 2 | ||||||
| 1964/1965 | FA Cup 2nd Rd | Luton Town | 1-0 | Gillingham | 0 | 0 | 1 | 0 | 1 | ||||||
| FA Cup 1st Rd Replay | Gillingham | 1-0 | Guildford City | 1 | 0 | 0 | 1 | 0 | |||||||
| FA Cup 1st Rd | Guildford City | 2-2 | Gillingham | 0 | 1 | 0 | 2 | 2 | |||||||
| 1963/1964 | FA Cup 1st Rd | Queen's Park Rangers | 4-1 | Gillingham | 0 | 0 | 1 | 1 | 4 | ||||||
| 1962/1963 | FA Cup 3rd Rd | Gillingham | 2-4 | Port Vale | 0 | 0 | 1 | 2 | 4 | ||||||
| FA Cup 2nd Rd | Gillingham | 3-0 | Bedford Town | 1 | 0 | 0 | 3 | 0 | |||||||
| FA Cup 1st Rd | Andover | 0-1 | Gillingham | 1 | 0 | 0 | 1 | 0 | |||||||
| 1961/1962 | FA Cup 1st Rd | Coventry City | 2-0 | Gillingham | 0 | 0 | 1 | 0 | 2 | ||||||
| 1960/1961 | FA Cup 3rd Rd | Gillingham | 2-6 | Leyton Orient | 0 | 0 | 1 | 2 | 6 | ||||||
| FA Cup 2nd Rd | Gillingham | 3-2 | Southend United | 1 | 0 | 0 | 3 | 2 | |||||||
| FA Cup 1st Rd | Ashford Town | 1-2 | Gillingham | 1 | 0 | 0 | 2 | 1 | |||||||
| 1959/1960 | FA Cup 3rd Rd | Gillingham | 1-4 | Swansea City | 0 | 0 | 1 | 1 | 4 | ||||||
| FA Cup 2nd Rd Replay | Torquay United | 1-2 | Gillingham | 1 | 0 | 0 | 2 | 1 | |||||||
| FA Cup 2nd Rd | Gillingham | 2-2 | Torquay United | 0 | 1 | 0 | 2 | 2 | |||||||
| FA Cup 1st Rd | Bedford Town | 0-4 | Gillingham | 1 | 0 | 0 | 4 | 0 | |||||||
| 1958/1959 | FA Cup 1st Rd Replay | Gillingham | 1-4 | Plymouth Argyle | 0 | 0 | 1 | 1 | 4 | ||||||
| FA Cup 1st Rd | Plymouth Argyle | 2-2 | Gillingham | 0 | 1 | 0 | 2 | 2 | |||||||
| 1957/1958 | FA Cup 3rd Rd | Nottingham Forest | 2-0 | Gillingham | 0 | 0 | 1 | 0 | 2 | ||||||
| FA Cup 2nd Rd Replay | Gillingham | 6-1 | Millwall | 1 | 0 | 0 | 6 | 1 | |||||||
| FA Cup 2nd Rd | Millwall | 1-1 | Gillingham | 0 | 1 | 0 | 1 | 1 | |||||||
| FA Cup 1st Rd | Gillingham | 10-1 | Gorleston | 1 | 0 | 0 | 10 | 1 | |||||||
| 1956/1957 | FA Cup 2nd Rd | Gillingham | 1-2 | Newport County | 0 | 0 | 1 | 1 | 2 | ||||||
| FA Cup 1st Rd Replay | Gillingham | 2-0 | Yiewsley | 1 | 0 | 0 | 2 | 0 | |||||||
| FA Cup 1st Rd | Yiewsley | 2-2 | Gillingham | 0 | 1 | 0 | 2 | 2 | |||||||
| 1955/1956 | FA Cup 1st Rd Replay | Shrewsbury Town | 4-1 | Gillingham | 0 | 0 | 1 | 1 | 4 | ||||||
| FA Cup 1st Rd | Gillingham | 1-1 | Shrewsbury Town | 0 | 1 | 0 | 1 | 1 | |||||||
| 1954/1955 | FA Cup 2nd Rd Replay | Reading | 5-3 | Gillingham | 0 | 0 | 1 | 3 | 5 | ||||||
| FA Cup 2nd Rd | Gillingham | 1-1 | Reading | 0 | 1 | 0 | 1 | 1 | |||||||
| FA Cup 1st Rd | Gillingham | 2-0 | Newport County | 1 | 0 | 0 | 2 | 0 | |||||||
| 1953/54 | FA Cup 1st Rd | Walthamstow Avenue | 1-0 | Gillingham | 0 | 0 | 1 | 0 | 1 | ||||||
| 1952/1953 | FA Cup 2nd Rd | Stockport County | 3-1 | Gillingham | 0 | 0 | 1 | 1 | 3 | ||||||
| FA Cup 1st Rd Replay | Gillingham | 3-0 | Wellington | 1 | 0 | 0 | 3 | 0 | |||||||
| FA Cup 1st Rd | Wellington | 1-1 | Gillingham | 0 | 1 | 0 | 1 | 1 | |||||||
| 1951/1952 | FA Cup 2nd Rd | Gillingham | 0-3 | Rochdale | 0 | 0 | 1 | 0 | 3 | ||||||
| FA Cup 1st Rd | Crystal Palace | 0-1 | Gillingham | 1 | 0 | 0 | 1 | 0 | |||||||
| 1950/1951 | FA Cup 2nd Rd 2nd Replay | Bristol Rovers | 2-1 | Gillingham | 0 | 0 | 1 | 1 | 2 | ||||||
| at Tottenham | |||||||||||||||
| FA Cup 2nd Rd Replay | Gillingham | 1-1 | Bristol Rovers | 0 | 1 | 0 | 1 | 1 | |||||||
| FA Cup 2nd Rd | Bristol Rovers | 2-2 | Gillingham | 0 | 1 | 0 | 2 | 2 | |||||||
| FA Cup 1st Rd | Linby CW | 1-4 | Gillingham | 1 | 0 | 0 | 4 | 1 | |||||||
| 1949/50 | FA Cup 2nd Rd | Yeovil Town | 3-1 | Gillingham | 0 | 0 | 1 | 1 | 3 | ||||||
| FA Cup 1st Rd | Hastings United | 1-3 | Gillingham | 1 | 0 | 0 | 3 | 1 | |||||||
| FA Cup 4th Qual Rd | Guildford City | 2-3 | Gillingham | 1 | 0 | 0 | 3 | 2 | |||||||
| 1948/49 | FA Cup 4th Qual Rd | Romford | 2-1 | Gillingham | 0 | 0 | 1 | 1 | 2 | ||||||
| 1947/1948 | FA Cup 3rd Rd Replay | Queen's Park Rangers | 3-1 | Gillingham | 0 | 0 | 1 | 1 | 3 | ||||||
| FA Cup 3rd Rd | Gillingham | 1-1 | Queen's Park Rangers | 0 | 1 | 0 | 1 | 1 | |||||||
| FA Cup 2nd Rd Replay | Gillingham | 3-0 | Rochdale | 1 | 0 | 0 | 3 | 0 | |||||||
| FA Cup 2nd Rd | Rochdale | 1-1 | Gillingham | 0 | 1 | 0 | 1 | 1 | |||||||
| FA Cup 1st Rd | Gillingham | 1-0 | Leyton Orient | 1 | 0 | 0 | 1 | 0 | |||||||
| FA Cup 4th Qualifying Rd | Gillingham | 3-1 | Barnet | 1 | 0 | 0 | 3 | 1 | |||||||
| 1946/1947 | FA Cup 3rd Rd | Swansea City | 4-1 | Gillingham | 0 | 0 | 1 | 1 | 4 | ||||||
| FA Cup 2nd Rd | Bristol City | 1-2 | Gillingham | 1 | 0 | 0 | 2 | 1 | |||||||
| FA Cup 1st Rd | Gillingham | 4-1 | Gravesend & Northfleet | 1 | 0 | 0 | 4 | 1 | |||||||
| FA Cup 4th Qual Rd | Guildford City | 1-2 | Gillingham | 1 | 0 | 0 | 2 | 1 | |||||||
| 1945/46 | FA Cup 4th Qual Rd | Gillingham | 3-9 | Sutton United | 0 | 0 | 1 | 3 | 9 | ||||||
| 1939-1945 | No Competition | ||||||||||||||
| 1938/39 | FA Cup 4th Qual Rd | Gillingham | 2-4 | Tunbridge Wells Rangers | 0 | 0 | 1 | 2 | 4 | ||||||
| 1937/1938 | FA Cup 1st Rd | Gillingham | 3-4 | Swindon Town | 0 | 0 | 1 | 3 | 4 | ||||||
| 1936/1937 | FA Cup 2nd Rd | Wrexham | 2-0 | Gillingham | 0 | 0 | 1 | 0 | 2 | ||||||
| FA Cup 1st Rd | Ryde Sports | 1-5 | Gillingham | 1 | 0 | 0 | 5 | 1 | |||||||
| 1935/1936 | FA Cup 2nd Rd | Crewe Alexandra | 2-1 | Gillingham | 0 | 0 | 1 | 1 | 2 | ||||||
| FA Cup 1st Rd | Exeter City | 0-4 | Gillingham | 1 | 0 | 0 | 4 | 0 | |||||||
| 1934/1935 | FA Cup 1st Rd | Bristol City | 2-0 | Gillingham | 0 | 0 | 1 | 0 | 2 | ||||||
| 1933/1934 | FA Cup 2nd Rd | Charlton Athletic | 1-0 | Gillingham | 0 | 0 | 1 | 0 | 1 | ||||||
| FA Cup 1st Rd | Oxford City | 1-5 | Gillingham | 1 | 0 | 0 | 5 | 1 | |||||||
| 1932/1933 | FA Cup 2nd Rd Replay | Gillingham | 1-3 | Bristol Rovers | 0 | 0 | 1 | 1 | 3 | ||||||
| FA Cup 2nd Rd | Bristol Rovers | 1-1 | Gillingham | 0 | 1 | 0 | 1 | 1 | |||||||
| FA Cup 1st Rd Replay | Wycombe Wanderers | 2-4 | Gillingham | 1 | 0 | 0 | 4 | 2 | |||||||
| FA Cup 1st Rd | Gillingham | 1-1 | Wycombe Wanderers | 0 | 1 | 0 | 1 | 1 | |||||||
| 1931/1932 | FA Cup 1st Rd | Bristol Rovers | 5-1 | Gillingham | 0 | 0 | 1 | 1 | 5 | ||||||
| 1930/1931 | FA Cup 2nd Rd | Gillingham | 1-3 | Aldershot Town | 0 | 0 | 1 | 1 | 3 | ||||||
| FA Cup 1st Rd | Gillingham | 7-2 | Guildford City | 1 | 0 | 0 | 7 | 2 | |||||||
| 1929/30 | FA Cup 1st Rd | Gillingham | 0-2 | Margate | 0 | 0 | 1 | 0 | 2 | ||||||
| 1928/1929 | FA Cup 1st Rd Replay | Torquay United | 5-1 | Gillingham | 0 | 0 | 1 | 1 | 5 | ||||||
| FA Cup 1st Rd | Gillingham | 0-0 | Torquay United | 0 | 1 | 0 | 0 | 0 | |||||||
| 1927/1928 | FA Cup 3rd Rd | Stoke City | 6-1 | Gillingham | 0 | 0 | 1 | 1 | 6 | ||||||
| FA Cup 2nd Rd | Gillingham | 2-0 | Southend United | 1 | 0 | 0 | 2 | 0 | |||||||
| FA Cup 1st Rd | Gillingham | 2-1 | Plymouth Argyle | 1 | 0 | 0 | 2 | 1 | |||||||
| 1926/1927 | FA Cup 2nd Rd Replay | Brentford | 1-0 | Gillingham | 0 | 0 | 1 | 0 | 1 | ||||||
| FA Cup 2nd Rd | Gillingham | 1-1 | Brentford | 0 | 1 | 0 | 1 | 1 | |||||||
| FA Cup 1st Rd Replay | Gillingham | 2-0 | Barking | 1 | 0 | 0 | 2 | 0 | |||||||
| FA Cup 1st Rd | Barking | 0-0 | Gillingham | 0 | 1 | 0 | 0 | 0 | |||||||
| 1925/1926 | FA Cup 2nd Rd | Southend United | 1-0 | Gillingham | 0 | 0 | 1 | 0 | 1 | ||||||
| FA Cup 1st Rd | Gillingham | 6-0 | Southall | 1 | 0 | 0 | 6 | 0 | |||||||
| 1924/1925 | FA Cup 6th Qualifying Rd 4th Replay | Gillingham | 1-2 | Barrow | 0 | 0 | 1 | 1 | 2 | ||||||
| at Millwall | |||||||||||||||
| FA Cup 6th Qualifying Rd 3rd Replay | Gillingham | 1-1 | Barrow | 0 | 1 | 0 | 1 | 1 | |||||||
| at Arsenal | |||||||||||||||
| FA Cup 6th Qualifying Rd 2nd Replay | Barrow | 1-1 | Gillingham | 0 | 1 | 0 | 1 | 1 | |||||||
| at Wolverhampton | |||||||||||||||
| FA Cup 6th Qualifying Rd 1st Replay | Barrow | 1-1 | Gillingham | 0 | 1 | 0 | 1 | 1 | |||||||
| FA Cup 6th Qualifying Rd | Gillingham | 0-0 | Barrow | 0 | 1 | 0 | 0 | 0 | |||||||
| FA Cup 5th Qual Rd Replay | Gillingham | 6-2 | Kettering Town | 1 | 0 | 0 | 6 | 2 | |||||||
| FA Cup 5th Qual Rd | Kettering Town | 1-1 | Gillingham | 0 | 1 | 0 | 1 | 1 | |||||||
| 1923/1924 | FA Cup 1st Rd Replay | Gillingham | 0-2 | Cardiff City | 0 | 0 | 1 | 0 | 2 | ||||||
| FA Cup 1st Rd | Cardiff City | 0-0 | Gillingham | 0 | 1 | 0 | 0 | 0 | |||||||
| FA Cup 6th Qualifying Rd | Gillingham | 1-0 | Tranmere Rovers | 1 | 0 | 0 | 1 | 0 | |||||||
| FA Cup 5th Qual Rd | Nunhead | 0-6 | Gillingham | 1 | 0 | 0 | 6 | 0 | |||||||
| 1922/23 | FA Cup 6th Qual Rd | Gillingham | 1-4 | Blyth Spartans | 0 | 0 | 1 | 1 | 4 | ||||||
| FA Cup 5th Qual Rd | London Caledonians | 1-2 | Gillingham | 1 | 0 | 0 | 2 | 1 | |||||||
| 1921/1922 | FA Cup 1st Rd | Gillingham | 1-3 | Oldham Athletic | 0 | 0 | 1 | 1 | 3 | ||||||
| FA Cup 6th Qual Rd | Gillingham | 3-1 | St. Albans | 1 | 0 | 0 | 3 | 1 | |||||||
| FA Cup 5th Qual Rd Replay | Gillingham | 3-1 | Northfleet | 1 | 0 | 0 | 3 | 1 | |||||||
| FA Cup 5th Qual Rd | Northfleet | 0-0 | Gillingham | 0 | 1 | 0 | 0 | 0 | |||||||
| 1920/1921 | FA Cup 6th Qualifying Rd | Northampton Town | 3-1 | Gillingham | 0 | 0 | 1 | 1 | 3 | ||||||
| FA Cup 5th Qual Rd | Gillingham | 2-1 | Dulwich Hamlet | 1 | 0 | 0 | 2 | 1 | |||||||
| FA Cup 4th Qualifying Rd | Gillingham | 1-0 | Maidstone United | 1 | 0 | 0 | 1 | 0 | |||||||
| 1919/20 | FA Cup 1st Rd | West Stanley | 3-1 | Gillingham | 0 | 0 | 1 | 1 | 3 | ||||||
| FA Cup 6th Qualifying Rd 3rd Replay | Gillingham | 3-1 | Swansea City | 1 | 0 | 0 | 3 | 1 | |||||||
| at Chelsea | |||||||||||||||
| FA Cup 6th Qualifying Rd 2nd Replay | Swansea City | 0-0 | Gillingham | 0 | 1 | 0 | 0 | 0 | |||||||
| at Cardiif | |||||||||||||||
| FA Cup 6th Qualifying Rd 1st Replay | Swansea City | 1-1 | Gillingham | 0 | 1 | 0 | 1 | 1 | |||||||
| FA Cup 6th Qualifying Rd | Gillingham | 1-1 | Swansea City | 0 | 1 | 0 | 1 | 1 | |||||||
| 1915-1919 | No competition | ||||||||||||||
| 1914/1915 | FA Cup 1st Rd | Rochdale | 2-0 | Gillingham | 0 | 0 | 1 | 0 | 2 | ||||||
| 1913/1914 | FA Cup 2nd Rd | Liverpool | 2-0 | Gillingham | 0 | 0 | 1 | 0 | 2 | ||||||
| FA Cup 1st Rd | Gillingham | 1-0 | Blackpool | 1 | 0 | 0 | 1 | 0 | |||||||
| FA Cup 5th Qualifying Rd | Gillingham | 1-0 | Watford | 1 | 0 | 0 | 1 | 0 | |||||||
| FA Cup 4th Qual Rd | Gillingham | 2-0 | Nunhead | 1 | 0 | 0 | 2 | 0 | |||||||
| 1912/1913 | FA Cup 1st Rd Replay | Barnsley | 3-1 | Gillingham | 0 | 0 | 1 | 1 | 3 | ||||||
| FA Cup 1st Rd | Gillingham | 0-0 | Barnsley | 0 | 1 | 0 | 0 | 0 | |||||||
| FA Cup 5th Qual Rd Replay | Gillingham | 3-0 | Spennymoor United | 1 | 0 | 0 | 3 | 0 | |||||||
| FA Cup 5th Qual Rd | Spennymoor United | 1-1 | Gillingham | 0 | 1 | 0 | 1 | 1 | |||||||
| 1911/12 | FA Cup 4th Qual Rd | Gillingham | 1-2 | Croydon Common | 0 | 0 | 1 | 1 | 2 | ||||||
| 1910/1911 | FA Cup 1st Rd | Gillingham | 0-1 | Bradford City | 0 | 0 | 1 | 0 | 1 | ||||||
| FA Cup 5th Qual Rd | Gillingham | 4-1 | Catford Southend | 1 | 0 | 0 | 4 | 1 | |||||||
| FA Cup 4th Qual Rd Replay | Gillingham | 7-0 | Royal Engineers (Aldershot) | 1 | 0 | 0 | 7 | 0 | |||||||
| FA Cup 4th Qual Rd | Royal Engineers (Aldershot) | 2-2 | Gillingham | 0 | 1 | 0 | 2 | 2 | |||||||
| 1909/10 | FA Cup 1st Rd 2nd Replay | Gillingham | 0-1 | Leyton | 0 | 0 | 1 | 0 | 1 | ||||||
| at Tottenham | |||||||||||||||
| FA Cup 1st Rd 1st Replay | Gillingham | 2-2 | Leyton | 0 | 1 | 0 | 2 | 2 | |||||||
| FA Cup 1st Rd | Leyton | 0-0 | Gillingham | 0 | 1 | 0 | 0 | 0 | |||||||
| FA Cup 5th Qualifying Rd | Rotherham Town | 0-1 | Gillingham | 1 | 0 | 0 | 1 | 0 | |||||||
| FA Cup 4th Qual Rd | Gillingham | 9-1 | Oxford City | 1 | 0 | 0 | 9 | 1 | |||||||
| 1908/09 | FA Cup 6th Qual Rd Replay | Gillingham | 2-1 | Hastings & St. Leonards | 1 | 0 | 0 | 2 | 1 | ||||||
| FA Cup 6th Qual Rd | Hastings & St. Leonards | 2-2 | Gillingham | 0 | 1 | 0 | 2 | 2 | |||||||
| 1907/1908 | FA Cup 2nd Rd Replay | Gillingham | 1-2 | Manchester City | 0 | 0 | 1 | 1 | 2 | ||||||
| FA Cup 2nd Rd | Manchester City | 1-1 | Gillingham | 0 | 1 | 0 | 1 | 1 | |||||||
| FA Cup 1st Rd | Gillingham | 3-1 | Sunderland | 1 | 0 | 0 | 3 | 1 | |||||||
| FA Cup 6th Qual Rd | Gillingham | 6-0 | Shepherds Bush | 1 | 0 | 0 | 6 | 0 | |||||||
| 1906/1907 | FA Cup 2nd Rd | Bury | 1-0 | Gillingham | 0 | 0 | 1 | 0 | 1 | ||||||
| FA Cup 1st Rd 2nd Replay | Gillingham | 2-0 | Burton United | 1 | 0 | 0 | 2 | 0 | |||||||
| at Fulham | |||||||||||||||
| FA Cup 1st Rd 1st Replay | Gillingham | 0-0 | Burton United | 0 | 1 | 0 | 0 | 0 | |||||||
| abandoned in extra time | |||||||||||||||
| FA Cup 1st Rd | Burton United | 0-0 | Gillingham | 0 | 1 | 0 | 0 | 0 | |||||||
| 1905/1906 | FA Cup 2nd Rd Replay | Southampton | 1-0 | Gillingham | 0 | 0 | 1 | 0 | 1 | ||||||
| FA Cup 2nd Rd | Gillingham | 0-0 | Southampton | 0 | 1 | 0 | 0 | 0 | |||||||
| FA Cup 1st Rd | Gillingham | 2-1 | Northampton Town | 1 | 0 | 0 | 2 | 1 | |||||||
| 1904/1905 | FA Cup 1st Rd | Gillingham | 0-1 | Brighton & Hove Albion | 0 | 0 | 1 | 0 | 1 | ||||||
| FA Cup 6th Qual Rd | Leyton | 2-6 | Gillingham | 1 | 0 | 0 | 6 | 2 | |||||||
| 1903/1904 | FA Cup 6th Qual Rd Replay | Bristol City | 5-2 | Gillingham | 0 | 0 | 1 | 2 | 5 | ||||||
| FA Cup 6th Qualifying Rd | Gillingham | 1-1 | Bristol City | 0 | 1 | 0 | 1 | 1 | |||||||
| 1902/03 | FA Cup 6th Qual Rd | Gillingham | 1-2 | Glossop North End | 0 | 0 | 1 | 1 | 2 | ||||||
| FA Cup 5th Qual Rd | Gillingham | 4-1 | Ilford | 1 | 0 | 0 | 4 | 1 | |||||||
| FA Cup 4th Qualifying Rd | Maidstone United | 0-3 | Gillingham | 1 | 0 | 0 | 3 | 0 | |||||||
| FA Cup 3rd Qual Rd | Gillingham | 2-0 | Leyton | 1 | 0 | 0 | 2 | 0 | |||||||
| 1901/1902 | FA Cup 6th Qualifying Rd | Walsall | 2-0 | Gillingham | 0 | 0 | 1 | 0 | 2 | ||||||
| FA Cup 5th Qual Rd | Gillingham | 1-0 | Grays United | 1 | 0 | 0 | 1 | 0 | |||||||
| FA Cup 4th Qual Rd Replay | Gillingham | 2-0 | Leyton | 1 | 0 | 0 | 2 | 0 | |||||||
| FA Cup 4th Qual Rd | Leyton | 2-2 | Gillingham | 0 | 1 | 0 | 2 | 2 | |||||||
| FA Cup 3rd Qual Rd | Gillingham | 6-1 | Ilford | 1 | 0 | 0 | 6 | 1 | |||||||
| 1900/1901 | FA Cup 4th Qualifying Rd Replay | West Ham United | 4-1 | Gillingham | 0 | 0 | 1 | 1 | 4 | ||||||
| FA Cup 4th Qualifying Rd | Gillingham | 1-1 | West Ham United | 0 | 1 | 0 | 1 | 1 | |||||||
| FA Cup 3rd Qual Rd | Grays United | 0-2 | Gillingham | 1 | 0 | 0 | 2 | 0 | |||||||
| 1899/1900 | FA Cup 4th Qualifying Rd Replay | Thames Ironworks | 2-0 | Gillingham | 0 | 0 | 1 | 0 | 2 | ||||||
| FA Cup 4th Qualifying Rd | Gillingham | 0-0 | Thames Ironworks | 0 | 1 | 0 | 0 | 0 | |||||||
| FA Cup 3rd Qualifying Rd 4th Replay | Woolwich Arsenal | 0-1 | Gillingham | 1 | 0 | 0 | 1 | 0 | |||||||
| at Gravesend | |||||||||||||||
| FA Cup 3rd Qualifying Rd 3rd Replay | Gillingham | 1-1 | Woolwich Arsenal | 0 | 1 | 0 | 1 | 1 | |||||||
| at Tottenham | |||||||||||||||
| FA Cup 3rd Qualifying Rd 2nd Replay | Woolwich Arsenal | 2-2 | Gillingham | 0 | 1 | 0 | 2 | 2 | |||||||
| at Millwall | |||||||||||||||
| FA Cup 3rd Qualifying Rd 1st Replay | Woolwich Arsenal | 0-0 | Gillingham | 0 | 1 | 0 | 0 | 0 | |||||||
| FA Cup 3rd Qualifying Rd | Gillingham | 1-1 | Woolwich Arsenal | 0 | 1 | 0 | 1 | 1 | |||||||
| 1898/1899 | FA Cup 1st Rd | Gillingham | 0-1 | Southampton | 0 | 0 | 1 | 0 | 1 | ||||||
| FA Cup 5th Qual Rd Replay | Gillingham | 2-0 | Gravesend United | 1 | 0 | 0 | 2 | 0 | |||||||
| FA Cup 5th Qual Rd | Gravesend United | 1-1 | Gillingham | 0 | 1 | 0 | 1 | 1 | |||||||
| FA Cup 4th Qual Rd | Gillingham | 2-1 | Sheppey United | 1 | 0 | 0 | 2 | 1 | |||||||
| FA Cup 3rd Qual Rd | Gillingham | 3-0 | Grays United | 1 | 0 | 0 | 3 | 0 | |||||||
| 1897/98 | FA Cup 5th Qualifying Rd | Woolwich Arsenal | 4-2 | Gillingham | 0 | 0 | 1 | 2 | 4 | ||||||
| FA Cup 4th Qual Rd | Gillingham | 1-0 | Chatham Town | 1 | 0 | 0 | 1 | 0 | |||||||
| FA Cup 3rd Qual Rd | Gillingham | 6-2 | Grays United | 1 | 0 | 0 | 6 | 2 | |||||||
| FA Cup 2nd Qual Rd | Gillingham | 2-0 | Eastbourne Swifts | 1 | 0 | 0 | 2 | 0 | |||||||
| FA Cup 1st Qual Rd | Northfleet | 1-3 | Gillingham | 1 | 0 | 0 | 3 | 1 | |||||||
| 1896/97 | FA Cup 4th Qual Rd | Northfleet | 3-1 | Gillingham | 0 | 0 | 1 | 1 | 3 | ||||||
| FA Cup 3rd Qual Rd | Gravesend | 1-4 | Gillingham | 1 | 0 | 0 | 4 | 1 | |||||||
| FA Cup 2nd Qual Rd | Gillingham | 6-1 | Faversham | 1 | 0 | 0 | 6 | 1 | |||||||
| 1895/1896 | FA Cup 2nd Qualifying Rd | Gillingham | 0-1 | Millwall Athletic | 0 | 0 | 1 | 0 | 1 | ||||||
| 1894/1895 | FA Cup 3rd Qualifying Rd | Gillingham | 0-2 | Millwall Athletic | 0 | 0 | 1 | 0 | 2 | ||||||
| FA Cup 2nd Qual Rd | Gillingham | 3-0 | Chatham Town | 1 | 0 | 0 | 3 | 0 | |||||||
| 1893/94 | FA Cup 1st Qual Rd | Ilford | 6-3 | Gillingham | 0 | 0 | 1 | 3 | 6 | ||||||
| 291 | 118 | 71 | 102 | 493 | 410 | ||||||||||