FA Cup 2023/24, Fourth Qualifying Round |
 | 14.10.2023 | | Weston-super-Mare | – | Maidenhead United | | 0:3 (0:2) |
| Weston-super-Mare |
FA Cup 2022/23, Fourth Qualifying Round |
| 15.10.2022 | | Maidenhead United | – | Eastbourne Borough | | 2:1 (1:0) |
| Maidenhead |
FA Cup 2021/22, Fourth Qualifying Round |
| 16.10.2021 | | Maidenhead United | – | Hastings United | | 3:1 (2:1) |
| Maidenhead |
FA Cup 2019/20, Fourth Qualifying Round |
| 22.10.2019 | | Wealdstone | – | Maidenhead United | | 0:2 (0:1) * |
| London |
FA Cup 2018/19, Fourth Qualifying Round |
| 23.10.2018 | | Maidenhead United | – | Chippenham Town | | 1:0 (0:0) * |
| Maidenhead |
FA Cup 2017/18, Fourth Qualifying Round |
| 14.10.2017 | | Maidenhead United | – | Havant & Waterlooville | | 2:1 (1:0) |
| Maidenhead |
FA Cup 2015/16, Fourth Qualifying Round |
| 24.10.2015 | | Maidenhead United | – | Woking | | 3:0 (1:0) |
| Maidenhead |
FA Cup 2015/16, Third Qualifying Round |
| 10.10.2015 | | | – | Maidenhead United | | 0:1 (0:0) |
| Blackfield |
FA Cup 2015/16, Second Qualifying Round |
| 29.09.2015 | | Maidenhead United | – | Winchester City | | 4:2 (2:1) * |
| Maidenhead |
FA Cup 2014/15, Second Qualifying Round |
| 27.09.2014 | | Maidenhead United | – | Faversham Town | | 4:0 |
| Maidenhead |
FA Cup 2012/13, Second Qualifying Round |
| 22.09.2012 | | Maidenhead United | – | Bognor Regis Town | | 4:2 |
| Maidenhead |
FA Cup 2011/12, Fourth Qualifying Round |
| 29.10.2011 | | Godalming Town | – | Maidenhead United | | 0:5 (0:2) |
| |
FA Cup 2011/12, Third qualifying round |
| 15.10.2011 | | Maidenhead United | – | Woking | | 4:1 (4:1) |
| |
FA Cup 2011/12, Second Qualifying Round |
| 05.10.2011 | | Farnborough | – | Maidenhead United | | 2:3 * |
| |
FA Cup 2010/11, Third Qualifying Round |
| 09.10.2010 | | Cinderford Town | – | Maidenhead United | | 0:4 |
| |
FA Cup 2010/11, Second Qualifying Round |
| 25.09.2010 | | Maidenhead United | – | Truro City | | 1:0 |
| |
FA Cup 2007/08, Fourth Qualifying Round |
| 27.10.2007 | | Maidenhead United | – | Hayes & Yeading United | | 1:0 (1:0) |
| |
FA Cup 2007/08, Third Qualifying Round |
| 13.10.2007 | | Maidenhead United | – | Shortwood United | | 3:0 |
| |
FA Cup 2007/08, Second Qualifying Round |
| 29.09.2007 | | Brockenhurst | – | Maidenhead United | | 0:6 |
| |
FA Cup 2006/07, Fourth Qualifying Round |
| 28.10.2006 | | Maidenhead United | – | Merthyr Tydfil | | 1:0 (0:0) |
| |
FA Cup 2006/07, Third Qualifying Round |
| 14.10.2006 | | Maidenhead United | – | Worthing United | | 3:1 |
| |
FA Cup 2006/07, Second Qualifying Round |
| 30.09.2006 | | East Thurrock United | – | Maidenhead United | | 1:2 |
| |
FA Cup 2006/07, First Qualifying Round |
| 19.09.2006 | | Carterton | – | Maidenhead United | | 2:3 * |
| |
FA Cup 2004/05, Third Qualifying Round |
| | | Maidenhead United | – | Windsor & Eton | | 2:1 (1:0) |
| |
FA Cup 1999/00, Second Qualifying Round |
| | | Walton & Hersham | – | Maidenhead United | | 0:2 |
| |
FA Cup 1999/00, First Qualifying Round |
| | | Maidenhead United | – | Viking Greenford | | 5:0 |
| |
FA Cup 1999/00, Preliminary Round |
| | | Whitehawk | – | Maidenhead United | | 0:1 |
| |
FA Cup 1998/99, Second Qualifying Round |
| | | Uxbridge | – | Maidenhead United | | 0:5 |
| |
FA Cup 1998/99, First Qualifying Round |
| | | Maidenhead United | – | Selsey | | 2:1 |
| |
FA Cup 1998/99, Preliminary Round |
| | | Abingdon Town | – | Maidenhead United | | 0:3 |
| |
FA Cup 1992/93, First Qualifying Round |
| | | Maidenhead United | – | Buckingham Town | | 2:1 * |
| |
FA Cup 1991/92, Second Qualifying Round |
| | | Maidenhead United | – | Bashley | | 1:0 * |
| |
FA Cup 1991/92, First Qualifying Round |
| | | Newport IOW | – | Maidenhead United | | 0:3 |
| |
FA Cup 1991/92, Preliminary Round |
| | | Sholing Sports | – | Maidenhead United | | 0:6 |
| |
FA Cup 1989/90, Second Qualifying Round |
| | | Maidenhead United | – | Stroud | | 2:0 |
| |
FA Cup 1989/90, First Qualifying Round |
| | | Banbury United | – | Maidenhead United | | 1:3 |
| |
FA Cup 1984/85, Preliminary Round |
| | | Southall | – | Maidenhead United | | 1:2 |
| |
FA Cup 1982/83, First Qualifying Round |
| | | Maidenhead United | – | Chichester City | | 4:2 |
| |
FA Cup 1981/82, First Qualifying Round |
| | | Egham Town | – | Maidenhead United | | 1:2 |
| |
FA Cup 1980/81, Second Qualifying Round |
| | | Maidenhead United | – | Harefield United | | 5:1 * |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Maidenhead United | – | Thame United | | 1:0 |
| |
FA Cup 1979/80, Third Qualifying Round |
| | | Metropolitan Police | – | Maidenhead United | | 0:1 |
| |
FA Cup 1979/80, Second Qualifying Round |
| | | Hendon | – | Maidenhead United | | 0:3 * |
| |
FA Cup 1979/80, First Qualifying Round |
| | | Maidenhead United | – | Clapton | | 1:0 |
| |
FA Cup 1977/78, First Qualifying Round |
| | | Maidenhead United | – | Windsor & Eton | | 3:0 |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Biggleswade Town | – | Maidenhead United | | 0:1 |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Maidenhead United | – | Windsor & Eton | | 4:1 |
| |
FA Cup 1973/74, Second Qualifying Round |
| | | Gravesend & Northfleet | – | Maidenhead United | | 2:3 |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Dorking | – | Maidenhead United | | 0:2 |
| |
FA Cup 1973/74, Preliminary Round |
| | | Maidenhead United | – | Hemel Hempstead | | 2:0 |
| |
FA Cup 1971/72, Fourth Qualifying Round |
| | | Maidenhead United | – | Walton & Hersham | | 2:1 |
| |
FA Cup 1971/72, Third Qualifying Round |
| | | Maidenhead United | – | Aveley | | 3:2 * |
| |
FA Cup 1971/72, Second Qualifying Round |
| | | Maidenhead United | – | Leytonstone | | 1:0 |
| |
FA Cup 1971/72, First Qualifying Round |
| | | Maidenhead United | – | Wycombe Wanderers | | 2:0 |
| |
FA Cup 1968/69, First Qualifying Round |
| | | Maidenhead United | – | Bletchley Town | | 1:0 * |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Maidenhead United | – | Aylesbury United | | 4:2 * |
| |
FA Cup 1966/67, First Qualifying Round |
| | | Maidenhead United | – | Grays Athletic | | 3:1 * |
| |
FA Cup 1963/64, Fourth Qualifying Round |
| | | Ilford | – | Maidenhead United | | 1:3 |
| |
FA Cup 1963/64, Third Qualifying Round |
| | | Maidenhead United | – | Hemel Hempstead | | 2:1 |
| |
FA Cup 1963/64, Second Qualifying Round |
| | | Banbury Spencer | – | Maidenhead United | | 2:3 |
| |
FA Cup 1963/64, First Qualifying Round |
| | | Aylesbury United | – | Maidenhead United | | 2:3 |
| |
FA Cup 1962/63, Fourth Qualifying Round |
| | | Maidenhead United | – | Tilbury | | 2:1 |
| |
FA Cup 1962/63, Third Qualifying Round |
| | | Maidenhead United | – | Finchley | | 3:1 |
| |
FA Cup 1962/63, Second Qualifying Round |
| | | Maidenhead United | – | Yiewsley | | 3:2 |
| |
FA Cup 1962/63, First Qualifying Round |
| | | Maidenhead United | – | Windsor & Eton | | 2:1 |
| |
FA Cup 1961/62, Second Qualifying Round |
| | | Maidenhead United | – | Edgware Town | | 1:0 |
| |
FA Cup 1961/62, First Qualifying Round |
| | | Maidenhead United | – | Hayes | | 8:2 |
| |
FA Cup 1960/61, Fourth Qualifying Round |
| | | Harrow Town | – | Maidenhead United | | 2:3 |
| |
FA Cup 1960/61, Third Qualifying Round |
| | | Edgware Town | – | Maidenhead United | | 0:2 * |
| |
FA Cup 1960/61, Second Qualifying Round |
| | | Maidenhead United | – | Uxbridge | | 4:0 |
| |
FA Cup 1960/61, First Qualifying Round |
| | | Windsor & Eton | – | Maidenhead United | | 2:4 |
| |
FA Cup 1959/60, Second Qualifying Round |
| | | Maidenhead United | – | Wokingham Town | | 5:0 |
| |
FA Cup 1959/60, First Qualifying Round |
| | | Maidenhead United | – | Abingdon Town | | 3:1 * |
| |
FA Cup 1959/60, Preliminary Round |
| | | Maidenhead United | – | Huntley & Palmers | | 4:1 |
| |
FA Cup 1958/59, Second Qualifying Round |
| | | Maidenhead United | – | Wokingham Town | | 4:0 |
| |
FA Cup 1958/59, First Qualifying Round |
| | | Maidenhead United | – | Witney Town | | 7:2 |
| |
FA Cup 1958/59, Preliminary Round |
| | | Abingdon Town | – | Maidenhead United | | 0:2 |
| |
FA Cup 1956/57, Preliminary Round |
| | | Maidenhead United | – | Huntley & Palmers | | 5:1 |
| |
FA Cup 1955/56, Preliminary Round |
| | | Marlow | – | Maidenhead United | | 1:2 |
| |
FA Cup 1954/55, Second Qualifying Round |
| | | Maidenhead United | – | Chesham United | | 5:3 * |
| |
FA Cup 1954/55, First Qualifying Round |
| | | Maidenhead United | – | Bicester Town | | 3:2 |
| |
FA Cup 1954/55, Preliminary Round |
| | | Marlow | – | Maidenhead United | | 0:2 * |
| |
FA Cup 1953/54, First Qualifying Round |
| | | Witney Town | – | Maidenhead United | | 0:1 |
| |
FA Cup 1953/54, Preliminary Round |
| | | Bicester Town | – | Maidenhead United | | 0:5 |
| |
FA Cup 1952/53, First Qualifying Round |
| | | Maidenhead United | – | Bicester Town | | 2:0 |
| |
FA Cup 1952/53, Preliminary Round |
| | | Maidenhead United | – | Banbury Spencer | | 3:0 * |
| |
FA Cup 1951/52, Preliminary Round |
| | | Maidenhead United | – | Yiewsley | | 4:1 |
| |
FA Cup 1950/51, Extra Preliminary Round |
| | | Maidenhead United | – | Windsor & Eton | | 2:1 * |
| |
FA Cup 1948/49, First Qualifying Round |
| | | Wallingford Town | – | Maidenhead United | | 1:3 |
| |
FA Cup 1948/49, Preliminary Round |
| | | Chesham United | – | Maidenhead United | | 1:4 |
| |
FA Cup 1947/48, First Qualifying Round |
| | | Maidenhead United | – | Huntley & Palmers | | 5:2 |
| |
FA Cup 1947/48, Preliminary Round |
| | | Maidenhead United | – | Lyons Club | | 7:2 |
| |
FA Cup 1947/48, Extra Preliminary Round |
| | | Marlow | – | Maidenhead United | | 0:2 |
| |
FA Cup 1946/47, Preliminary Round |
| | | Maidenhead United | – | Yiewsley | | 3:0 * |
| |
FA Cup 1946/47, Extra Preliminary Round |
| | | Hounslow Town | – | Maidenhead United | | 1:4 |
| |
FA Cup 1886/87, First Round |
| 30.10.1886 | | South Reading | – | Maidenhead | | 0:2 |
| |
FA Cup 1881/82, Second Round |
| 03.12.1881 | | Maidenhead | – | Acton | | 2:1 |
| |
FA Cup 1881/82, First Round |
| 22.10.1881 | | Henley | – | Maidenhead | | 0:2 |
| |
FA Cup 1880/81, First Round |
| 20.11.1880 | | Old Harrovians | – | Maidenhead | | 0:1 * |
| |
FA Cup 1879/80, Second Round |
| 23.11.1879 | | Henley | – | Maidenhead | | 1:3 |
| |
FA Cup 1879/80, First Round |
| 25.10.1879 | | Maidenhead | – | Calthorpe | | 3:1 |
| |
FA Cup 1877/78, First Round |
| 27.10.1877 | | Maidenhead | – | Reading Hornets | | 10:0 |
| |
FA Cup 1875/76, First Round |
| 23.10.1875 | | Maidenhead | – | Ramblers | | 2:0 |
| |
FA Cup 1874/75, Second Round |
| 05.12.1874 | | Maidenhead | – | Reigate Priory | | 2:1 |
| |
FA Cup 1874/75, First Round |
| 14.11.1874 | | Hitchin | – | Maidenhead | | 0:1 |
| |
FA Cup 1873/74, Second Round |
| 22.11.1873 | | Maidenhead | – | High Wycombe | | 1:0 |
| |
FA Cup 1872/73, Third Round |
| 21.12.1872 | | Windsor Home Park | – | Maidenhead | | 0:1 |
| |
FA Cup 1872/73, Second Round |
| 23.11.1872 | | 1st Surrey Rifles | – | Maidenhead | | 0:3 |
| |
FA Cup 1872/73, First Round |
| 26.10.1872 | | Maidenhead | – | Marlow | | 1:0 |
| |
FA Cup 1871/72, First Round |
| 11.11.1871 | | Maidenhead | – | Marlow | | 2:0 |
| |
FA Cup 1873/74, First Round |
| | | Maidenhead | – | Civil Service | | +:- |
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