| Tottenham Hotspur FC v West Bromwich Albion FC 04/04/1958 | £10.99 | |
| Chelsea FC v Tottenham Hotspur FC 27/08/1958 | £8.00 | |
| Manchester United FC v Tottenham Hotspur FC 20/09/1958 | £10.50 | |
| Arsenal FC v Tottenham Hotspur FC 05/09/1959 | £10.50 | |
| Tottenham Hotspur FC v West Ham United FC 09/09/1959 | £13.99 | |
| West Ham United FC v Tottenham Hotspur FC 14/09/1959 | £7.00 | |
| Manchester City FC v Tottenham Hotspur FC 31/10/1959 | £10.00 | |
| Manchester City FC v Tottenham Hotspur FC 31/10/1959 | £7.50 | |
| Fulham FC v Tottenham Hotspur FC 12/12/1959 | £5.00 | |
| Leeds United FC v Tottenham Hotspur FC 26/12/1959 | £34.99 | |
| Tottenham Hotspur FC v Manchester City FC 16/04/1960 | £8.50 | |
| Aston Villa FC v Tottenham Hotspur FC 11/02/1961 | £25.00 |