| Woodlands | | 2019 | | Preliminary Round | 01-09-2019 | | Arnold Town | Woodlands | 1-4 | | 1st Qualifying Round | 22-09-2019 | | Woodlands | Hykeham Town | 2-1 | | 2nd Qualifying Round | 17-10-2019 | | Woodlands | Rise Park | 2-1 | | 3rd Qualifying Round | 27-10-2019 | | Bedworth United | Woodlands | 2-4 | | First Round | 17-11-2019 | | Woodlands | Billericay Town | 0-13 | |
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| 2020 | | Extra Preliminary Round | 06-09-2020 | | AFC Leicester | Woodlands | 0-5 | | Preliminary Round | 20-09-2020 | | Woodlands | Oadby & Wigston | 0-2 | | 2021 | | 2nd Qualifying Round | 03-10-2021 | | Woodlands | Anstey Nomads | 0-5 | | Borrowash Victoria | | 2022 | | 2nd Qualifying Round | 02-10-2022 | | Leicester City Ladies | Borrowash Victoria | 8-0 | | 2023 | | 1st Qualifying Round | 10-09-2023 | | Whitchurch Alport | Borrowash Victoria | 4-3 | | 2024 | | 1st Qualifying Round | 01-09-2024 | | Borrowash Victoria | Tamworth | 2-1 | | 2nd Qualifying Round | 22-09-2024 | | Alvechurch | Borrowash Victoria | 5-1 | | Melbourne Dynamos |
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