| 1. Ronde | 03.08.2019 | Coventry City | - | Southend United | 1:0 | ||||
| 2. Ronde | 10.08.2019 | Southend United | - | Blackpool FC | 1:3 | ||||
| 3. Ronde | 17.08.2019 | Lincoln City | - | Southend United | 4:0 |  |
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| 4. Ronde | 20.08.2019 | Southend United | - | Peterborough United | 0:2 | ||||
| 5. Ronde | 24.08.2019 | Wycombe Wanderers | - | Southend United | 4:3 | ||||
| 12. Ronde | 05.10.2019 | Gillingham FC | - | Southend United | 3:1 | ||||
| 13. Ronde | 12.10.2019 | Southend United | - | AFC Wimbledon | 1:4 | ||||
| 14. Ronde | 18.10.2019 | Tranmere Rovers | - | Southend United | 1:1 | |
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| 15. Ronde | 22.10.2019 | Southend United | - | Doncaster Rovers | 1:7 | ||||
| 16. Ronde | 26.10.2019 | Southend United | - | Ipswich Town | 1:3 | ||||
| 17. Ronde | 02.11.2019 | Sunderland AFC | - | Southend United | 1:0 | ||||
| 7. Ronde | 05.11.2019 | Portsmouth FC | - | Southend United | 4:1 | ||||
| 26. Ronde | 18.02.2020 | Southend United | - | Gillingham FC | 0:1 | ||||
| 35. Ronde | 22.02.2020 | Southend United | - | Burton Albion | 2:3 | ||||
| 36. Ronde | 29.02.2020 | Oxford United | - | Southend United | 2:1 | ||||
| 37. Ronde | 07.03.2020 | Southend United | - | Bristol Rovers | 3:1 |
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