| Pen Mill | | 2011 | | First Qualifying Round | 02-10-2011 | | Pen Mill | St Nicholas | 1-2 | | 2012 | | First Qualifying Round | 30-09-2012 | | Pen Mill | Bitton | 3-5 | | 2013 | | First Qualifying Round | 22-09-2013 | | Cheltenham Town | Pen Mill | 9-0 | | 2014 | | First Qualifying Round | 28-09-2014 | | Pen Mill | Bridgwater Town | 0-5 | | 2015 | | First Qualifying Round | 06-09-2015 | | Wimborne Town | Pen Mill | 8-0 | | 2016 | | Second Qualifying Round | 18-09-2016 | | Downend Flyers | Pen Mill | 7-1 | | 2017 | | Second Qualifying Round | 17-09-2017 | | Pen Mill | Forest Green Rovers | 1-4 | | 2020 | | Preliminary Round | 20-09-2020 | | Pen Mill | Ilminster Town | O-W | | 2022 | | First Qualifying Round | 18-09-2022 | | Pen Mill | Longwell Green | 10-0 | | Second Qualifying Round | 02-10-2022 | | Pen Mill | Pucklechurch Sports | 1-5 | | 2023 | | Second Qualifying Round | 01-10-2023 | | Pen Mill | Forest Green Rovers | O-W | |
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