| Maidstone United | | 2012 | | First Qualifying Round | 30-09-2012 | | Rusthall | Maidstone United | 1-4 | | Second Qualifying Round | 14-10-2012 | | London Corinthians | Maidstone United | 14-0 | | 2013 | | First Qualifying Round | 22-09-2013 | | London Corinthians | Maidstone United | 2-0 | | 2014 | | First Qualifying Round | 28-09-2014 | | Maidstone United | Battersea & Wandsworth | W/O | | Second Qualifying Round | 12-10-2014 | | Carshalton Athletic | Maidstone United | 5-2 | |
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| 2021 | | Second Qualifying Round | 03-10-2021 | | Maidstone United | Bromley | 0-7 | | 2022 | | First Qualifying Round | 18-09-2022 | | Maidstone United | Herne Bay | 1-5 | | 2023 | | First Qualifying Round | 10-09-2023 | | Margate | Maidstone United | 6-0 | | 2024 | | First Qualifying Round | 01-09-2024 | | Maidstone United | Tooting Bec | 1-4 |
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