| Harlow Town | | 2016 | | 2nd Qualifying Round | 18-09-2016 | | Harlow Town | Billericay Town | 2-3 | | 2017 | | 1st Qualifying Round | 03-09-2017 | | Harlow Town | Little Thurrock Dynamos | 4-0 | | 2nd Qualifying Round | 17-09-2017 | | Harlow Town | Bungay Town | 3-2 | | 3rd Qualifying Round | 08-10-2017 | | Harlow Town | Denham United | 1-0 | | First Round | 12-11-2017 | | Harlow Town | Royston Town | 2-1 | | Second Round | 03-12-2017 | | Luton Town | Harlow Town | 3-2 | |
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| 2018 | | 1st Qualifying Round | 02-09-2018 | | Brentwood Town | Harlow Town | 1-2 | | 2nd Qualifying Round | 30-09-2018 | | Cambridge United | Harlow Town | 6-0 | | 2019 | | Preliminary Round | 01-09-2019 | | AFC Sudbury | Harlow Town | 0-8 | | 1st Qualifying Round | 22-09-2019 | | Harlow Town | King's Lynn Town | 3-1 | | 2nd Qualifying Round | 06-10-2019 | | Harlow Town | Wroxham | 4-3 | | 3rd Qualifying Round | 27-10-2019 | | Harlow Town | Billericay Town | 1-2 | |
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| 2020 | | Extra Preliminary Round | 06-09-2020 | | Runwell Sports | Harlow Town | 0-6 | | Preliminary Round | 20-09-2020 | | Colney Heath | Harlow Town | 3-4 | | 1st Qualifying Round | 04-10-2020 | | Bowers & Pitsea | Harlow Town | 0-1 | | 2nd Qualifying Round | 18-10-2020 | | Harlow Town | St Ives Town | 5-1 | | 3rd Qualifying Round | 01-11-2020 | | Harlow Town | Royston Town | 3-3 | | First Round | 13-12-2020 | | Harlow Town | Ipswich Town | 2-9 | |
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| 2021 | | 3rd Qualifying Round | 24-10-2021 | | Harlow Town | Norwich City | 0-2 | | 2022 | | 2nd Qualifying Round | 02-10-2022 | | Harlow Town | Garston | W/O | | 3rd Qualifying Round | 23-10-2022 | | Harlow Town | Bowers & Pitsea | 1-1 | |
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