| Carlisle United | | 2014 | | Preliminary Round | 07-09-2014 | | Carlisle United | CMB | 2-3 | | 2015 | | First Qualifying Round | 06-09-2015 | | Carlisle United | Burnley | 1-3 | | 2016 | | Second Qualifying Round | 18-09-2016 | | Norton & Stockton Ancients | Carlisle United | 7-0 | | 2017 | | First Qualifying Round | 03-09-2017 | | Carlisle United | Wallsend Boys Club | 3-1 | | Second Qualifying Round | 17-09-2017 | | Cramlington United | Carlisle United | 1-7 | | Third Qualifying Round | 08-10-2017 | | Newcastle United | Carlisle United | 9-1 | | 2018 | | Preliminary Round | 26-08-2018 | | Workington Reds | Carlisle United | 1-3 | | First Qualifying Round | 02-09-2018 | | Carlisle United | Bishop Auckland | 1-2 | | 2019 | | Preliminary Round | 01-09-2019 | | Carlisle United | Hartlepool United | 1-11 | | 2020 | | Preliminary Round | 20-09-2020 | | Sunderland West End | Carlisle United | 7-0 | | 2021 | | First Qualifying Round | 12-09-2021 | | West Allotment | Carlisle United | 9-0 | | 2022 | | Second Qualifying Round | 02-10-2022 | | Gateshead Rutherford | Carlisle United | 2-0 | | 2023 | | First Qualifying Round | 10-09-2023 | | Carlisle United | Hartlepool Pools Youth | 1-3 | | 2024 | | 1st Qualifying Round | 01-09-2024 | | Penrith AFC | Carlisle United | 18-2 |
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