| Chelsea FC v Tottenham Hotspur FC 27/08/1958 | £8.00 | |
| Tottenham Hotspur FC v Chelsea FC 03/09/1958 | £18.99 | |
| Manchester United FC v Tottenham Hotspur FC 20/09/1958 | £10.50 | |
| Tottenham Hotspur FC v West Ham United FC 26/12/1958 | £19.99 | |
| 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 | |
| Tottenham Hotspur FC v Norwich City FC 14/02/1959 | £12.99 | |
| Tottenham Hotspur FC v West Bromwich Albion FC 26/08/1959 | £17.99 | |
| 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 | |
| West Ham United FC v Tottenham Hotspur FC 14/09/1959 | £7.00 |