FA Cup 2019/20, Fourth Qualifying Round |
 | 19.10.2019 |  | Maidenhead United | – | Wealdstone | | 1:1 (0:0) |
| Maidenhead |
FA Cup 2018/19, Fourth Qualifying Round |
| 20.10.2018 | | Chippenham Town | – | Maidenhead United | | 1:1 (0:0) |
| Chippenham |
FA Cup 2015/16, First Round Proper |
| 08.11.2015 | | Port Vale | – | Maidenhead United | | 1:1 (1:0) |
| Stoke-on-Trent |
FA Cup 2015/16, Second Qualifying Round |
| 26.09.2015 | | Winchester City | – | Maidenhead United | | 1:1 (1:0) |
| Winchester |
FA Cup 2014/15, Third Qualifying Round |
| 11.10.2014 | | Maidenhead United | – | Gosport Borough | | 1:1 (1:1) |
| Maidenhead |
FA Cup 2011/12, First Round Proper |
| 12.11.2011 | | Maidenhead United | – | Aldershot Town | | 1:1 (1:0) |
| Maidenhead |
FA Cup 2011/12, Second Qualifying Round |
| 01.10.2011 | | Maidenhead United | – | Farnborough | | 1:1 (1:0) |
| Maidenhead |
FA Cup 2006/07, First Round Proper |
| 11.11.2006 | | Stafford Rangers | – | Maidenhead United | | 1:1 (1:0) |
| Stafford |
FA Cup 2006/07, First Qualifying Round |
| 16.09.2006 | | Maidenhead United | – | Carterton | | 1:1 |
| |
FA Cup 2004/05, Second Qualifying Round |
| | | Maidenhead United | – | Whitstable Town | | 1:1,
pen. 3:2 * |
| |
FA Cup 2004/05, Second Qualifying Round |
| | | Whitstable Town | – | Maidenhead United | | 0:0 |
| |
FA Cup 2001/02, Second Qualifying Round |
| | | Maidenhead United | – | Aldershot Town | | 1:1 |
| |
FA Cup 2000/01, Second Qualifying Round |
| | | Maidenhead United | – | Hitchin Town | | 1:1,
pen. 7:6 * |
| |
FA Cup 2000/01, Second Qualifying Round |
| | | Hitchin Town | – | Maidenhead United | | 1:1 |
| |
FA Cup 1992/93, First Qualifying Round |
| | | Buckingham Town | – | Maidenhead United | | 1:1 |
| |
FA Cup 1991/92, Third Qualifying Round |
| | | Horsham | – | Maidenhead United | | 1:1 |
| |
FA Cup 1991/92, Second Qualifying Round |
| | | Bashley | – | Maidenhead United | | 1:1 |
| |
FA Cup 1988/89, Preliminary Round |
| | | Sheppey United | – | Maidenhead United | | 1:1 |
| |
FA Cup 1987/88, Preliminary Round |
| | | Maidenhead United | – | Tunbridge Wells | | 1:1 |
| |
FA Cup 1983/84, First Qualifying Round |
| | | Fareham Town | – | Maidenhead United | | 1:1 |
| |
FA Cup 1982/83, Second Qualifying Round |
| | | Dorchester Town | – | Maidenhead United | | 1:1 |
| |
FA Cup 1980/81, Third Qualifying Round |
| | | Maidenhead United | – | Addlestone & Weybridge Town | | 0:0 |
| |
FA Cup 1980/81, Second Qualifying Round |
| | | Harefield United | – | Maidenhead United | | 0:0 |
| |
FA Cup 1979/80, Second Qualifying Round |
| | | Maidenhead United | – | Hendon | | 2:2 |
| |
FA Cup 1971/72, Third Qualifying Round |
| | | Aveley | – | Maidenhead United | | 1:1 |
| |
FA Cup 1968/69, First Qualifying Round |
| | | Bletchley Town | – | Maidenhead United | | 0:0 |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Aylesbury United | – | Maidenhead United | | 2:2 |
| |
FA Cup 1966/67, First Qualifying Round |
| | | Grays Athletic | – | Maidenhead United | | 0:0 |
| |
FA Cup 1960/61, Third Qualifying Round |
| | | Maidenhead United | – | Edgware Town | | 3:3 |
| |
FA Cup 1959/60, First Qualifying Round |
| | | Abingdon Town | – | Maidenhead United | | 1:1 |
| |
FA Cup 1954/55, Second Qualifying Round |
| | | Chesham United | – | Maidenhead United | | 5:5 |
| |
FA Cup 1954/55, Preliminary Round |
| | | Maidenhead United | – | Marlow | | 2:2 |
| |
FA Cup 1952/53, Preliminary Round |
| | | Banbury Spencer | – | Maidenhead United | | 1:1 |
| |
FA Cup 1950/51, Extra Preliminary Round |
| | | Windsor & Eton | – | Maidenhead United | | 1:1 |
| |
FA Cup 1949/50, Preliminary Round |
| | | Maidenhead United | – | Osberton Radiator | | 1:1 |
| |
FA Cup 1946/47, Preliminary Round |
| | | Yiewsley | – | Maidenhead United | | 3:3 |
| |
FA Cup 1880/81, First Round |
| 13.11.1880 | | Maidenhead | – | Old Harrovians | | 1:1 |
| |
FA Cup 1878/79, First Round |
| 19.10.1878 | | Barnes | – | Maidenhead | | 1:1 |
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