| West Ham United FC v Tottenham Hotspur FC 14/09/1959 | £7.00 | |
| Manchester City FC v Tottenham Hotspur FC 31/10/1959 | £7.50 | |
| Manchester City FC v Tottenham Hotspur FC 31/10/1959 | £5.50 | |
| Manchester City FC v Tottenham Hotspur FC 31/10/1959 | £10.00 | |
| Tottenham Hotspur FC v Tbilisi Dynamo 16/11/1959 | £16.99 | |
| Fulham FC v Tottenham Hotspur FC 12/12/1959 | £5.00 | |
| Tottenham Hotspur FC v Leicester City FC 13/02/1960 | £12.99 | |
| Chelsea FC v Tottenham Hotspur FC 15/04/1960 | £6.50 | |
| Tottenham Hotspur FC v Manchester City FC 16/04/1960 | £8.50 | |
| Tottenham Hotspur FC v Chelsea FC 18/04/1960 | £12.99 | |
| Wolverhampton Wanderers FC v Tottenham Hotspur FC 23/04/1960 | £5.99 | |
| Sheffield Wednesday FC v Tottenham Hotspur FC 12/11/1960 | £5.00 |