| Tottenham Hotspur FC v West Ham United FC 26/12/1958 | £19.99 | |
| Tottenham Hotspur FC v Blackburn Rovers FC 03/01/1959 | View match | |
| Tottenham Hotspur FC v West Ham United FC 10/01/1959 | £19.99 | |
| Tottenham Hotspur FC v West Ham United FC 10/01/1959 | £19.99 | |
| Newcastle United FC v Tottenham Hotspur FC 17/01/1959 | View match | |
| Tottenham Hotspur FC v Newport County 24/01/1959 | View match | |
| Tottenham Hotspur FC v Arsenal FC 31/01/1959 | View match | |
| Trowbridge Town v Tottenham Hotspur FC 31/01/1959 | View match | |
| Tottenham Hotspur FC v Manchester United FC 07/02/1959 | View match | |
| Tottenham Hotspur FC v Norwich City FC 14/02/1959 | £12.99 | |
| Norwich City FC v Tottenham Hotspur FC 18/02/1959 | View match | |
| Tottenham Hotspur FC v Portsmouth FC 21/02/1959 | View match |