25. Round | 03/01/1959 | Portsmouth FC | - | Nottingham Forest | 0:1 | ||||
26. Round | 17/01/1959 | Chelsea FC | - | Portsmouth FC | 2:2 | ||||
27. Round | 31/01/1959 | Portsmouth FC | - | Blackpool FC | 1:2 | ||||
28. Round | 07/02/1959 | Blackburn Rovers | - | Portsmouth FC | 2:1 | ||||
30. Round | 21/02/1959 | Tottenham Hotspur | - | Portsmouth FC | 4:4 | ||||
31. Round | 28/02/1959 | Leeds United | - | Portsmouth FC | 1:1 | ||||
32. Round | 07/03/1959 | Portsmouth FC | - | Manchester City | 3:4 | ||||
29. Round | 11/03/1959 | Portsmouth FC | - | Newcastle United | 1:5 | ||||
36. Round | 28/03/1959 | Leicester City | - | Portsmouth FC | 3:1 | ||||
37. Round | 30/03/1959 | Portsmouth FC | - | Manchester United | 1:3 | ||||
38. Round | 04/04/1959 | Portsmouth FC | - | Preston North End | 1:2 | ||||
39. Round | 11/04/1959 | Burnley FC | - | Portsmouth FC | 2:1 | ||||
41. Round | 15/04/1959 | Portsmouth FC | - | Everton FC | 2:3 | ||||
40. Round | 18/04/1959 | Portsmouth FC | - | Bolton Wanderers | 0:1 | ||||
33. Round | 22/04/1959 | Luton Town | - | Portsmouth FC | 3:1 | ||||
42. Round | 25/04/1959 | Arsenal FC | - | Portsmouth FC | 5:2 |