2. Round | 25/08/1958 | Aston Villa | - | Portsmouth FC | 3:2 | ||||
3. Round | 30/08/1958 | Nottingham Forest | - | Portsmouth FC | 5:0 | ||||
14. Round | 25/10/1958 | Portsmouth FC | - | Luton Town | 2:2 | ||||
35. Round | 27/03/1959 | Manchester United | - | Portsmouth FC | 6:1 | ||||
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 |