| Sherwood | | 2018 | | Preliminary Round | 26-08-2018 | | Oadby & Wigston | Sherwood | 6-0 | | 2019 | | Preliminary Round | 01-09-2019 | | Sherwood | Arnold Eagles | 0-7 | | 2020 | | Extra Preliminary Round | 06-09-2020 | | Sherwood | HBW United | W/O | | Preliminary Round | 20-09-2020 | | Belper Town | Sherwood | 0-3 | | 1st Qualifying Round | 04-10-2020 | | Redditch United | Sherwood | 4-0 | | 2021 |  | | 1st Qualifying Round | 12-09-2021 | | Sherwood | Kettering Town | 0-3 | | 2022 | | 2nd Qualifying Round | 02-10-2022 | | Sherwood | Rugby Town | 1-0 | | 3rd Qualifying Round | 23-10-2022 | | Crewe Alexandra | Sherwood | 8-0 | | 2023 | | 1st Qualifying Round | 10-09-2023 | | Sherwood | Moulton | 2-0 | | 2nd Qualifying Round | 01-10-2023 | | Sherwood | Beaumont Park | 0-0 | |
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| 2024 | | 1st Qualifying Round | 01-09-2024 | | Moulton | Sherwood | 1-5 | | 2nd Qualifying Round | 22-09-2024 | | Sherwood | River City | 0-3 |
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