FA Cup 2023/24, First Round Proper |
 | 04.11.2023 |  | Oxford United | – | Maidenhead United | | 2:0 (1:0) |
| Oxford |
FA Cup 2022/23, First Round Proper |
| 05.11.2022 | | Maidenhead United | – | Dagenham & Redbridge | | 0:1 (0:0) |
| Maidenhead |
FA Cup 2021/22, First Round Proper |
| 06.11.2021 | | Halifax Town | – | Maidenhead United | | 7:4 (4:3) |
| Halifax |
FA Cup 2020/21, Fourth Qualifying Round |
| 24.10.2020 | | Maidenhead United | – | Cray Valley Paper Mills | | 2:3 |
| Maidenhead |
FA Cup 2019/20, First Round Proper |
| 09.11.2019 | | Maidenhead United | – | Rotherham United | | 1:3 (1:0) |
| Maidenhead |
FA Cup 2018/19, First Round Proper |
| 10.11.2018 | | Maidenhead United | – | Portsmouth | | 0:4 (0:1) |
| Maidenhead |
FA Cup 2017/18, First Round Proper |
| 05.11.2017 | | Coventry City | – | Maidenhead United | | 2:0 (2:0) |
| Coventry |
FA Cup 2016/17, Second Qualifying Round |
| 17.09.2016 | | Staines Town | – | Maidenhead United | | 1:0 |
| Staines |
FA Cup 2015/16, First Round Proper |
| 19.11.2015 | | Maidenhead United | – | Port Vale | | 1:3 (1:1) * |
| Maidenhead |
FA Cup 2014/15, Third Qualifying Round |
| 14.10.2014 | | Gosport Borough | – | Maidenhead United | | 3:0 (1:0) * |
| Gosport |
FA Cup 2013/14, Second Qualifying Round |
| 28.09.2013 | | Oxford City | – | Maidenhead United | | 1:0 |
| Marston |
FA Cup 2012/13, Third Qualifying Round |
| 06.10.2012 | | Didcot Town | – | Maidenhead United | | 1:0 (1:0) |
| Didcot |
FA Cup 2011/12, First Round Proper |
| 22.11.2011 | | Aldershot Town | – | Maidenhead United | | 2:0 (2:0) * |
| Aldershot |
FA Cup 2010/11, Fourth Qualifying Round |
| 23.10.2010 | | Forest Green Rovers | – | Maidenhead United | | 1:0 |
| Nailsworth |
FA Cup 2009/10, Second Qualifying Round |
| 26.09.2009 | | Maidenhead United | – | Truro City | | 2:5 |
| |
FA Cup 2008/09, Second Qualifying Round |
| 27.09.2008 | | Bashley | – | Maidenhead United | | 2:1 |
| |
FA Cup 2007/08, First Round Proper |
| 10.11.2007 | | Horsham | – | Maidenhead United | | 4:1 (1:0) |
| Horsham |
FA Cup 2006/07, First Round Proper |
| 21.11.2006 | | Maidenhead United | – | Stafford Rangers | | 0:2 (0:1) * |
| Maidenhead |
FA Cup 2005/06, Second Qualifying Round |
| 24.09.2005 | | Yeading | – | Maidenhead United | | 3:0 |
| |
FA Cup 2004/05, Fourth Qualifying Round |
| | | Aldershot Town | – | Maidenhead United | | 2:1 (1:0) |
| |
FA Cup 2003/04, Second Qualifying Round |
| | | Dover Athletic | – | Maidenhead United | | 4:0 |
| |
FA Cup 2002/03, Second Qualifying Round |
| | | Maidenhead United | – | Welling United | | 1:2 |
| |
FA Cup 2001/02, Second Qualifying Round |
| | | Aldershot Town | – | Maidenhead United | | 1:0 * |
| |
FA Cup 2000/01, Third Qualifying Round |
| | | Hucknall Town | – | Maidenhead United | | 3:2 |
| |
FA Cup 1999/00, Third Qualifying Round |
| | | Maidenhead United | – | Salisbury City | | 0:1 |
| |
FA Cup 1998/99, Third Qualifying Round |
| | | Maidenhead United | – | Kingstonian | | 2:4 |
| |
FA Cup 1997/98, Preliminary Round |
| | | Newport AFC | – | Maidenhead United | | 2:1 |
| |
FA Cup 1996/97, Preliminary Round |
| | | Maidenhead United | – | Havant Town | | 0:1 |
| |
FA Cup 1995/96, Preliminary Round |
| | | Thame United | – | Maidenhead United | | 4:0 |
| |
FA Cup 1994/95, Preliminary Round |
| | | Maidenhead United | – | Havant Town | | 0:1 |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Maidenhead United | – | Newbury Town | | 1:2 |
| |
FA Cup 1992/93, Second Qualifying Round |
| | | Abingdon Town | – | Maidenhead United | | 2:0 |
| |
FA Cup 1991/92, Third Qualifying Round |
| | | Maidenhead United | – | Horsham | | 0:1 * |
| |
FA Cup 1990/91, First Qualifying Round |
| | | Wycombe Wanderers | – | Maidenhead United | | 3:0 |
| |
FA Cup 1989/90, Third Qualifying Round |
| | | Abingdon Town | – | Maidenhead United | | 3:1 |
| |
FA Cup 1988/89, Preliminary Round |
| | | Maidenhead United | – | Sheppey United | | 0:1 * |
| |
FA Cup 1987/88, Preliminary Round |
| | | Tunbridge Wells | – | Maidenhead United | | 4:3 * |
| |
FA Cup 1986/87, Preliminary Round |
| | | Redhill | – | Maidenhead United | | 3:2 |
| |
FA Cup 1985/86, Preliminary Round |
| | | Tilbury | – | Maidenhead United | | 2:0 |
| |
FA Cup 1984/85, First Qualifying Round |
| | | Maidenhead United | – | Potton United | | 0:2 |
| |
FA Cup 1983/84, First Qualifying Round |
| | | Maidenhead United | – | Fareham Town | | 0:1 * |
| |
FA Cup 1982/83, Second Qualifying Round |
| | | Maidenhead United | – | Dorchester Town | | 0:2 * |
| |
FA Cup 1981/82, Second Qualifying Round |
| | | Maidenhead United | – | Harrow Borough | | 0:2 |
| |
FA Cup 1980/81, Third Qualifying Round |
| | | Addlestone & Weybridge Town | – | Maidenhead United | | 5:0 * |
| |
FA Cup 1979/80, Fourth Qualifying Round |
| |  | Merthyr Tydfil | – | Maidenhead United | | 2:1 |
| |
FA Cup 1978/79, Preliminary Round |
| | | Farnborough Town | – | Maidenhead United | | 1:0 |
| |
FA Cup 1977/78, Second Qualifying Round |
| | | Feltham | – | Maidenhead United | | 3:2 |
| |
FA Cup 1976/77, Preliminary Round |
| | | Letchworth Garden City | – | Maidenhead United | | 5:1 |
| |
FA Cup 1975/76, Second Qualifying Round |
| | | Enfield | – | Maidenhead United | | 6:0 |
| |
FA Cup 1974/75, Second Qualifying Round |
| | | Wimbledon | – | Maidenhead United | | 4:0 |
| |
FA Cup 1973/74, Third Qualifying Round |
| | | Epping Town | – | Maidenhead United | | 3:0 |
| |
FA Cup 1972/73, First Qualifying Round |
| | | Maidenhead United | – | Woking | | 0:1 |
| |
FA Cup 1971/72, First Round Proper |
| 20.11.1971 | | Enfield | – | Maidenhead United | | 2:0 |
| |
FA Cup 1970/71, First Qualifying Round |
| | | Maidenhead United | – | Dunstable Town | | 0:1 |
| |
FA Cup 1969/70, Preliminary Round |
| | | Marlow | – | Maidenhead United | | 4:1 |
| |
FA Cup 1968/69, Second Qualifying Round |
| | | Aylesbury United | – | Maidenhead United | | 2:1 |
| |
FA Cup 1967/68, Second Qualifying Round |
| | | Maidenhead United | – | Banbury United | | 1:3 |
| |
FA Cup 1966/67, Second Qualifying Round |
| | | Maidenhead United | – | Leatherhead | | 0:2 |
| |
FA Cup 1965/66, First Qualifying Round |
| | | Oxford City | – | Maidenhead United | | 5:2 |
| |
FA Cup 1964/65, Fourth Qualifying Round |
| | | Guildford City | – | Maidenhead United | | 9:0 |
| |
FA Cup 1963/64, First Round Proper |
| 16.11.1963 | | Maidenhead United | – | Bath City | | 0:2 |
| |
FA Cup 1962/63, First Round Proper |
| 03.11.1962 | | Maidenhead United | – | Wycombe Wanderers | | 0:3 |
| |
FA Cup 1961/62, Third Qualifying Round |
| | | Maidenhead United | – | Yiewsley | | 2:3 |
| |
FA Cup 1960/61, First Round Proper |
| 05.11.1960 | | Colchester United | – | Maidenhead United | | 5:0 |
| |
FA Cup 1959/60, Third Qualifying Round |
| | | Oxford City | – | Maidenhead United | | 3:0 |
| |
FA Cup 1958/59, Third Qualifying Round |
| | | Maidenhead United | – | Headington United | | 1:6 |
| |
FA Cup 1957/58, Preliminary Round |
| | | Abingdon Town | – | Maidenhead United | | 1:0 |
| |
FA Cup 1956/57, First Qualifying Round |
| | | Maidenhead United | – | Oxford City | | 2:3 |
| |
FA Cup 1955/56, First Qualifying Round |
| | | Wycombe Wanderers | – | Maidenhead United | | 4:2 |
| |
FA Cup 1954/55, Third Qualifying Round |
| | | Oxford City | – | Maidenhead United | | 4:1 |
| |
FA Cup 1953/54, Second Qualifying Round |
| | | Headington United | – | Maidenhead United | | 4:0 |
| |
FA Cup 1952/53, Second Qualifying Round |
| | | Headington United | – | Maidenhead United | | 2:0 |
| |
FA Cup 1951/52, First Qualifying Round |
| | | St Albans City | – | Maidenhead United | | 3:1 |
| |
FA Cup 1950/51, Preliminary Round |
| | | Maidenhead United | – | Wycombe Wanderers | | 0:2 |
| |
FA Cup 1949/50, Preliminary Round |
| | | Osberton Radiator | – | Maidenhead United | | 1:0 * |
| |
FA Cup 1948/49, Second Qualifying Round |
| | | Oxford City | – | Maidenhead United | | 8:0 |
| |
FA Cup 1947/48, Second Qualifying Round |
| | | Banbury Spencer | – | Maidenhead United | | 4:0 |
| |
FA Cup 1946/47, First Qualifying Round |
| | | Uxbridge | – | Maidenhead United | | 2:1 |
| |
FA Cup 1945/46, Preliminary Round |
| | | Hayes | – | Maidenhead United | | 4:1 |
| |
FA Cup 1887/88, First Round |
| 15.10.1887 | | Swifts | – | Maidenhead | | 3:1 |
| |
FA Cup 1886/87, Second Round |
| 20.11.1886 | | Maidenhead | – | Dulwich | | 2:3 |
| |
FA Cup 1885/86, First Round |
| 31.10.1885 | | Brentwood | – | Maidenhead | | 3:0 |
| |
FA Cup 1884/85, First Round |
| 08.11.1884 | | Maidenhead | – | Old Wykehamists | | 0:3 |
| |
FA Cup 1883/84, First Round |
| 10.11.1883 | | West End | – | Maidenhead | | 1:0 |
| |
FA Cup 1882/83, First Round |
| 04.11.1882 | | Maidenhead | – | Old Westminsters | | 0:2 |
| |
FA Cup 1881/82, Fourth Round |
| 14.01.1882 | | Old Etonians | – | Maidenhead | | 6:3 |
| |
FA Cup 1880/81, Second Round |
| 11.12.1880 | | Grey Friars | – | Maidenhead | | 1:0 |
| |
FA Cup 1879/80, Fourth Round |
| 14.02.1880 | | Maidenhead | – | Oxford University | | 0:1 |
| |
FA Cup 1878/79, First Round |
| 09.11.1878 | | Maidenhead | – | Barnes | | 0:4 * |
| |
FA Cup 1877/78, Second Round |
| 08.12.1877 | | Cambridge University | – | Maidenhead | | 4:2 |
| |
FA Cup 1875/76, Second Round |
| 11.12.1875 | | Old Etonians | – | Maidenhead | | 8:0 |
| |
FA Cup 1874/75, Third Round |
| 23.01.1875 | | Old Etonians | – | Maidenhead | | 1:0 |
| |
FA Cup 1873/74, Third Round |
| 10.12.1873 | | Royal Engineers | – | Maidenhead | | 7:0 |
| |
FA Cup 1872/73, Fourth Round |
| 03.02.1873 | | Oxford University | – | Maidenhead | | 4:0 |
| |
FA Cup 1871/72, Second Round |
| 16.12.1871 | | Crystal Palace | – | Maidenhead | | 3:0 |
| |
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