| Southend United Community Sports Club |
| 2020 |
| Preliminary Round | 20-09-2020 | | Southend United Community Sports Club | Houghton Athletic | 1-1 |
| 1st Qualifying Round | 04-10-2020 | | Peterborough Northern Star | Southend United Community Sports Club | 10-0 |
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| 2021 |
| 1st Qualifying Round | 12-09-2021 | | Rayleigh Town | Southend United Community Sports Club | 1-5 |
| 2nd Qualifying Round | 03-10-2021 | | Garston | Southend United Community Sports Club | 2-3 |
| 3rd Qualifying Round | 24-10-2021 | | Southend United Community Sports Club | Frontiers | 3-0 |
| First Round | 14-11-2021 | | Hashtag United | Southend United Community Sports Club | 17-0 |
| 2022 |
| 1st Qualifying Round | 18-09-2022 | | Southend United Community Sports Club | Hertford Town | 4-2 |
| 1st Qualifying Round | 25-09-2022 | | Southend United Community Sports Club | Hertford Town | 0-1 |
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| 2023 |
| 1st Qualifying Round | 10-09-2023 | | Holland | Southend United Community Sports Club | 0-5 |
| 2nd Qualifying Round | 01-10-2023 | | Enfield Town | Southend United Community Sports Club | 8-2 |
| 2024 |
| 2nd Qualifying Round | 22-09-2024 | | Barking | Southend United Community Sports Club | 4-1 |
| Southend United |
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