| Sherborne Town | | 2019 | | Preliminary Round | 01-09-2019 | | Sherborne Town | Keynsham Town Development | 10-0 | | First Qualifying Round | 22-09-2019 | | Shanklin | Sherborne Town | 0-12 | | Second Qualifying Round | 06-10-2019 | | Exeter City | Sherborne Town | 7-1 | | 2020 | | Preliminary Round | 20-09-2020 | | Sherborne Town | Bournemouth Sports | 3-0 | | First Qualifying Round | 11-10-2020 | | Sherborne Town | Oldland Abbotonians | 2-1 | | Second Qualifying Round | 18-10-2020 | | Portishead Town | Sherborne Town | 2-0 | | 2021 | | Second Qualifying Round | 03-10-2021 | | Sherborne Town | Pucklechurch Sports | 4-1 | | Third Qualifying Round | 24-10-2021 | | Weymouth | Sherborne Town | 0-13 | | First Round | 14-11-2021 | | Ilminster Town | Sherborne Town | 3-0 | | 2022 | | Second Qualifying Round | 02-10-2022 | | Sherborne Town | Winchester City Flyers | 1-1 | |
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| 2023 | | Second Qualifying Round | 01-10-2023 | | Sherborne Town | Weymouth | 4-0 | | Third Qualifying Round | 22-10-2023 | | Downend Flyers | Sherborne Town | 1-4 | | First Round | 12-11-2023 | | Swindon Town | Sherborne Town | 6-0 |
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