Maidenhead United | 2008 | Preliminary Round | 07-09-2008 | | Maidenhead United | Chalfont St Peter | 5-1 | First Qualifying Round | 28-09-2008 | | Aylesbury United | Maidenhead United | 0-11 | Second Qualifying Round | 12-10-2008 | | Maidenhead United | Tetbury Town | 6-0 | Third Qualifying Round | 26-10-2008 | | Maidenhead United | Chinnor | 7-3 | First Round | 09-11-2008 | | Maidenhead United | Swindon Town | 0-1 | 2009 | First Qualifying Round | 27-09-2009 | | Maidenhead United | Banbury United | 14-0 | Second Qualifying Round | 11-10-2009 | | East Preston | Maidenhead United | 3-2 | |
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2010 | First Qualifying Round | 10-10-2010 | | Henley Town | Maidenhead United | 0-2 | Second Qualifying Round | 24-10-2010 | | Oxford United | Maidenhead United | 1-2 | Third Qualifying Round | 14-11-2010 | | Maidenhead United | Oxford City | 3-4 | 2011 | First Qualifying Round | 02-10-2011 | | Oxford United | Maidenhead United | 5-2 | 2012 | First Qualifying Round | 30-09-2012 | | Maidenhead United | Banbury United | 5-1 | Second Qualifying Round | 14-10-2012 | | Maidenhead United | Hemel Hempstead Town | 4-1 | Third Qualifying Round | 11-11-2012 | | Maidenhead United | Colne Valley | 2-3 | 2013 | First Qualifying Round | 22-09-2013 | | Maidenhead United | Newbury | 6-2 | Second Qualifying Round | 06-10-2013 | | Maidenhead United | Eastbourne Town | 5-1 | Third Qualifying Round | 03-11-2013 | | Maidenhead United | Fulham Foundation | 2-1 | First Round | 01-12-2013 | | Crystal Palace | Maidenhead United | 2-0 | 2014 | First Qualifying Round | 28-09-2014 | | Colne Valley | Maidenhead United | 1-6 | Second Qualifying Round | 12-10-2014 | | Maidenhead United | Old Actonians | 2-2 | Third Qualifying Round | 02-11-2014 | | Maidenhead United | Shanklin | 3-0 | First Round | 14-12-2014 | | C&K Basildon | Maidenhead United | 5-2 | |
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2015 | Third Qualifying Round | 11-10-2015 | | Brislington | Maidenhead United | 2-3 | Fourth Qualifying Round | 08-11-2015 | | Keynsham Town | Maidenhead United | 5-0 | 2016 | Third Qualifying Round | 09-10-2016 | | Gillingham | Maidenhead United | 4-0 | 2017 | Third Qualifying Round | 08-10-2017 | | Maidenhead United | Luton Town | 0-1 | 2018 | Second Qualifying Round | 23-09-2018 | | Whyteleafe | Maidenhead United | 2-0 | 2019 | Second Qualifying Round | 06-10-2019 | | Maidenhead United | Bowers & Pitsea | 1-2 | 2020 | Second Qualifying Round | 18-10-2020 | | Maidenhead United | Denham United | 1-0 | Third Qualifying Round | 01-11-2020 | | Fulham | Maidenhead United | 1-2 | First Round | 13-12-2020 | | Billericay Town | Maidenhead United | 4-0 | 2021 | Third Qualifying Round | 24-10-2021 | | Chesham United | Maidenhead United | 3-0 | 2022 | Third Qualifying Round | 23-10-2022 | | Fulham | Maidenhead United | 3-2 | 2023 | Third Qualifying Round | 22-10-2023 | | Richmond & Kew | Maidenhead United | 1-3 | First Round | 12-11-2023 | | Sutton United | Maidenhead United | 3-4 | Second Round | 03-12-2023 | | Southampton | Maidenhead United | 3-0 | |
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