| 1. Round | 03/08/2019 | Tranmere Rovers | - | Rochdale AFC | 2:3 |  |
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| 4. Round | 20/08/2019 | Bristol Rovers | - | Tranmere Rovers | 2:0 | ||||
| 6. Round | 31/08/2019 | Rotherham United | - | Tranmere Rovers | 1:1 | ||||
| 7. Round | 07/09/2019 | Tranmere Rovers | - | Gillingham FC | 2:2 | ||||
| 8. Round | 14/09/2019 | Oxford United | - | Tranmere Rovers | 3:0 | ||||
| 11. Round | 28/09/2019 | Ipswich Town | - | Tranmere Rovers | 4:1 | ||||
| 12. Round | 05/10/2019 | Tranmere Rovers | - | Shrewsbury Town | 0:1 | ||||
| 13. Round | 13/10/2019 | Coventry City | - | Tranmere Rovers | 0:1 |  |
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| 14. Round | 18/10/2019 | Tranmere Rovers | - | Southend United | 1:1 | ||||
| 15. Round | 22/10/2019 | Sunderland AFC | - | Tranmere Rovers | 5:0 | ||||
| 17. Round | 02/11/2019 | Milton Keynes Dons | - | Tranmere Rovers | 1:3 |  |
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| 18. Round | 17/11/2019 | Tranmere Rovers | - | Wycombe Wanderers | 0:2 | ||||
| 19. Round | 23/11/2019 | Fleetwood Town | - | Tranmere Rovers | 2:1 | ||||
| 20. Round | 07/12/2019 | Tranmere Rovers | - | Accrington Stanley | 1:1 | ||||
| 21. Round | 14/12/2019 | Lincoln City | - | Tranmere Rovers | 1:0 | ||||
| 22. Round | 21/12/2019 | Tranmere Rovers | - | AFC Wimbledon | 1:0 | |
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| 23. Round | 26/12/2019 | Burton Albion | - | Tranmere Rovers | 4:2 |
England
Jamaica