| 1. Round | 23/08/1958 | Wolverhampton Wanderers | - | Nottingham Forest | 5:1 | ||||
| 2. Round | 27/08/1958 | Nottingham Forest | - | Manchester United | 0:3 | ||||
| 3. Round | 30/08/1958 | Nottingham Forest | - | Portsmouth FC | 5:0 | ||||
| 5. Round | 06/09/1958 | Aston Villa | - | Nottingham Forest | 2:3 | ||||
| 6. Round | 10/09/1958 | Nottingham Forest | - | Tottenham Hotspur | 1:1 | ||||
| 30. Round | 21/02/1959 | Blackpool FC | - | Nottingham Forest | 1:0 | ||||
| 31. Round | 09/04/1959 | Luton Town | - | Nottingham Forest | 5:1 | ||||
| 26. Round | 20/04/1959 | Nottingham Forest | - | Aston Villa | 2:0 | ||||
| 41. Round | 22/04/1959 | Nottingham Forest | - | Leeds United | 0:3 | ||||
| 42. Round | 25/04/1959 | West Bromwich Albion | - | Nottingham Forest | 2:0 |
England