| Islington Borough | | 2018 | | Preliminary Round | 19-08-2018 | | Oakwood | Islington Borough | 0-4 | | 1st Qualifying Round | 02-09-2018 | | Hassocks | Islington Borough | 2-4 | | 2nd Qualifying Round | 23-09-2018 | | Worthing | Islington Borough | 1-5 | | 3rd Qualifying Round | 07-10-2018 | | Islington Borough | New London Lionesses | 1-2 | |
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| 2019 | | Preliminary Round | 01-09-2019 | | Sutton United | Islington Borough | 0-1 | | 1st Qualifying Round | 22-09-2019 | | Victoire | Islington Borough | 0-4 | | 2nd Qualifying Round | 06-10-2019 | | Enfield Town | Islington Borough | 4-0 | | 2020 | | Preliminary Round | 20-09-2020 | | Islington Borough | Ashford | 1-4 | | 2021 | | 2nd Qualifying Round | 03-10-2021 | | Islington Borough | Hastings United | 1-2 | | 2022 | | 1st Qualifying Round | 18-09-2022 | | Comets | Islington Borough | 3-4 | | 2nd Qualifying Round | 02-10-2022 | | Islington Borough | Dartford | 0-4 | | 2023 | | 2nd Qualifying Round | 01-10-2023 | | Islington Borough | Stanway Rovers | 5-3 | | 3rd Qualifying Round | 22-10-2023 | | Dussindale & Hellesdon Rovers | Islington Borough | 2-1 | | 2024 | | 1st Qualifying Round | 01-09-2024 | | Hertford Town | Islington Borough | 3-2 |
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