1. Round | 22/08/1959 | Chelsea FC | - | Preston North End | 4:4 | ||||
2. Round | 25/08/1959 | Preston North End | - | West Ham United | 1:1 | ||||
3. Round | 29/08/1959 | Preston North End | - | West Bromwich Albion | 1:1 | ||||
4. Round | 31/08/1959 | West Ham United | - | Preston North End | 2:1 | ||||
5. Round | 05/09/1959 | Newcastle United | - | Preston North End | 1:2 | ||||
6. Round | 08/09/1959 | Burnley FC | - | Preston North End | 2:1 | ||||
7. Round | 12/09/1959 | Preston North End | - | Birmingham City | 3:2 | ||||
8. Round | 15/09/1959 | Preston North End | - | Burnley FC | 1:0 | ||||
9. Round | 19/09/1959 | Tottenham Hotspur | - | Preston North End | 5:1 | ||||
16. Round | 07/11/1959 | Preston North End | - | Nottingham Forest | 1:0 |