| Ascot United | | 2012 | | First Qualifying Round | 30-09-2012 | | Oxford City | Ascot United | 5-0 | | 2013 | | First Qualifying Round | 22-09-2013 | | AFC Dunstable | Ascot United | 4-0 | | 2014 | | First Qualifying Round | 28-09-2014 | | Newbury | Ascot United | 1-0 | | 2015 | | First Qualifying Round | 06-09-2015 | | Marlow | Ascot United | 6-2 | | 2016 | | Second Qualifying Round | 18-09-2016 | | Ascot United | Milton Keynes City | 3-2 | | Third Qualifying Round | 09-10-2016 | | Leyton Orient | Ascot United | 16-0 | | 2017 | | First Qualifying Round | 03-09-2017 | | Ascot United | Newbury | 1-1 | | Second Qualifying Round | 17-09-2017 | | Ascot United | Chesham United | 0-2 | | 2018 | | First Qualifying Round | 02-09-2018 | | Wycombe Wanderers | Ascot United | 1-3 | | Second Qualifying Round | 23-09-2018 | | Ashford Town (Middx) | Ascot United | 11-2 | | 2019 | | Preliminary Round | 01-09-2019 | | Ascot United | Abingdon Town | 2-3 | | 2020 | | Preliminary Round | 20-09-2020 | | Ascot United | Swindon Supermarine | 6-0 | | First Qualifying Round | 04-10-2020 | | Ascot United | Denham United | 0-3 | | 2021 | | Second Qualifying Round | 03-10-2021 | | Ascot United | Tilehurst Panthers | 3-0 | | Third Qualifying Round | 24-10-2021 | | Ascot United | Oxford City | 4-0 | | First Round | 14-11-2021 | | Ascot United | Chichester & Selsey | 0-4 | | 2022 | | Second Qualifying Round | 02-10-2022 | | Milton United | Ascot United | 1-3 | | Third Qualifying Round | 23-10-2022 | | Ascot United | AFC Acorns | 5-0 | | First Round | 13-11-2022 | | Dartford | Ascot United | 2-2 | |
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| 2023 | | Second Qualifying Round | 01-10-2023 | | Ascot United | Wycombe Wanderers | 0-1 | | 2024 | | Second Qualifying Round | 22-09-2024 | | Ascot United | Denham United | 5-0 | | Third Qualifying Round | 13-10-2024 | | Ascot United | Woodley United | 8-2 | | First Round | 03-11-2024 | | Brentford | Ascot United | 4-2 |
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