| 9. Round | 13/09/2022 | Chesterfield FC | - | Southend United | 3:2 |  |
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| 10. Round | 17/09/2022 | Southend United | - | Wrexham AFC | 0:0 | ||||
| 11. Round | 24/09/2022 | Wealdstone FC | - | Southend United | 0:1 | |
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| 12. Round | 01/10/2022 | Southend United | - | Yeovil Town | 1:0 | ||||
| 13. Round | 04/10/2022 | Southend United | - | Woking FC | 1:1 | |
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| 14. Round | 08/10/2022 | Dagenham & Redbridge | - | Southend United | 1:1 |
Wales