| Preston North End FC v Tottenham Hotspur FC 25/04/1959 | View match | |
| Torpedo Club (Moscow) v Tottenham Hotspur FC 27/05/1959 | View match | |
| Russia v Tottenham Hotspur FC 04/06/1959 | View match | |
| Newcastle United FC v Tottenham Hotspur FC 22/08/1959 | View match | |
| Tottenham Hotspur FC v West Bromwich Albion FC 26/08/1959 | £17.99 | |
| Tottenham Hotspur FC v Birmingham City FC 29/08/1959 | View match | |
| West Bromwich Albion FC v Tottenham Hotspur FC 02/09/1959 | View match | |
| Arsenal FC v Tottenham Hotspur FC 05/09/1959 | £10.50 | |
| Tottenham Hotspur FC v West Ham United FC 09/09/1959 | £13.99 | |
| Tottenham Hotspur FC v West Ham United FC 09/09/1959 | £13.99 | |
| Manchester United FC v Tottenham Hotspur FC 12/09/1959 | View match | |
| West Ham United FC v Tottenham Hotspur FC 14/09/1959 | £7.00 |