1. Round | 22/08/1959 | Newcastle United | - | Tottenham Hotspur | 1:5 | ||||
2. Round | 26/08/1959 | Tottenham Hotspur | - | West Bromwich Albion | 2:2 | ||||
3. Round | 29/08/1959 | Tottenham Hotspur | - | Birmingham City | 0:0 | ||||
4. Round | 02/09/1959 | West Bromwich Albion | - | Tottenham Hotspur | 1:2 | ||||
5. Round | 05/09/1959 | Arsenal FC | - | Tottenham Hotspur | 1:1 | ||||
6. Round | 09/09/1959 | Tottenham Hotspur | - | West Ham United | 2:2 | ||||
7. Round | 12/09/1959 | Manchester United | - | Tottenham Hotspur | 1:5 | ||||
8. Round | 14/09/1959 | West Ham United | - | Tottenham Hotspur | 1:2 | ||||
9. Round | 19/09/1959 | Tottenham Hotspur | - | Preston North End | 5:1 | ||||
10. Round | 26/09/1959 | Leicester City | - | Tottenham Hotspur | 1:1 | ||||
11. Round | 03/10/1959 | Tottenham Hotspur | - | Burnley FC | 1:1 | ||||
12. Round | 10/10/1959 | Tottenham Hotspur | - | Wolverhampton Wanderers | 5:1 | ||||
14. Round | 24/10/1959 | Tottenham Hotspur | - | Nottingham Forest | 2:1 | ||||
15. Round | 31/10/1959 | Manchester City | - | Tottenham Hotspur | 1:2 |