| 13. Round | 15/10/1949 | Portsmouth FC | - | Derby County | 3:1 | ||||
| 14. Round | 22/10/1949 | West Bromwich Albion | - | Portsmouth FC | 3:0 | ||||
| 15. Round | 29/10/1949 | Portsmouth FC | - | Manchester United | 0:0 | ||||
| 30. Round | 18/02/1950 | Wolverhampton Wanderers | - | Portsmouth FC | 1:0 | ||||
| 31. Round | 25/02/1950 | Portsmouth FC | - | Birmingham City | 2:0 | ||||
| 32. Round | 08/03/1950 | Derby County | - | Portsmouth FC | 2:1 |  |
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| 33. Round | 11/03/1950 | Portsmouth FC | - | Burnley FC | 2:1 | ||||
| 34. Round | 18/03/1950 | Sunderland AFC | - | Portsmouth FC | 1:1 | ||||
| 35. Round | 25/03/1950 | Portsmouth FC | - | Chelsea FC | 4:0 | ||||
| 36. Round | 01/04/1950 | Stoke City | - | Portsmouth FC | 0:1 | ||||
| 37. Round | 07/04/1950 | Portsmouth FC | - | Fulham FC | 3:0 | ||||
| 38. Round | 08/04/1950 | Portsmouth FC | - | West Bromwich Albion | 0:1 | ||||
| 39. Round | 10/04/1950 | Fulham FC | - | Portsmouth FC | 0:1 | ||||
| 42. Round | 03/05/1950 | Arsenal FC | - | Portsmouth FC | 2:0 |
India