| Workington Reds | | 2012 | | 1st Qualifying Round | 07-10-2012 | | Workington Reds | Whitley Bay | 0-5 | | 2013 | | 1st Qualifying Round | 22-09-2013 | | Workington Reds | RACA Tynedale | 0-5 | | 2014 | | 1st Qualifying Round | 28-09-2014 | | Mersey Girls | Workington Reds | 2-1 | | 2015 | | 1st Qualifying Round | 06-09-2015 | | Workington Reds | Mersey Girls | 1-2 | | 2016 | | 2nd Qualifying Round | 18-09-2016 | | Workington Reds | Birtley Town | 2-1 | | 3rd Qualifying Round | 09-10-2016 | | Workington Reds | RACA Tynedale | 1-5 | | 2017 | | 1st Qualifying Round | 03-09-2017 | | Workington Reds | Redcar Town | 1-2 | | 2018 | | Preliminary Round | 26-08-2018 | | Workington Reds | Carlisle United | 1-3 | | 2019 | | Preliminary Round | 01-09-2019 | | Blyth Town | Workington Reds | 2-1 | | 2020 | | Extra Preliminary Round | 06-09-2020 | | Boro Rangers | Workington Reds | 0-1 | | Preliminary Round | 20-09-2020 | | Durham United | Workington Reds | 3-4 | | 1st Qualifying Round | 04-10-2020 | | Morecambe | Workington Reds | 5-2 | | 2021 | | 1st Qualifying Round | 12-09-2021 | | Durham United | Workington Reds | 1-4 | | 2nd Qualifying Round | 03-10-2021 | | Hartlepool United | Workington Reds | 7-2 | | 2022 | | 1st Qualifying Round | 18-09-2022 | | Workington Reds | Washington AFC | 1-1 | | 2nd Qualifying Round | 02-10-2022 | | Ponteland United | Workington Reds | 3-0 | | 2023 | | 2nd Qualifying Round | 01-10-2023 | | Workington Reds | Penrith AFC | 4-5 | | Workington Town | | 2024 | | 1st Qualifying Round | 01-09-2024 | | Workington Town | Gateshead | 4-1 | | 2nd Qualifying Round | 22-09-2024 | | Chester Le Street Town | Workington Town | 4-0 |
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