| Tottenham Hotspur FC v West Ham United FC 19/04/1969 | £3.00 | |
| Tottenham Hotspur FC v Southampton FC 22/04/1969 | £2.00 | |
| Leicester City FC v Tottenham Hotspur FC 29/04/1969 | £4.00 | |
| Leicester City FC v Tottenham Hotspur FC 29/04/1969 | £4.50 | |
| Tottenham Hotspur FC v Burnley FC 13/08/1969 | £2.50 | |
| Tottenham Hotspur FC v Liverpool FC 16/08/1969 | £6.00 | |
| Tottenham Hotspur FC v Liverpool FC 16/08/1969 | £4.00 | |
| Tottenham Hotspur FC v Liverpool FC 16/08/1969 | £4.00 | |
| West Ham United FC v Tottenham Hotspur FC 06/09/1969 | £4.00 | |
| West Ham United FC v Tottenham Hotspur FC 06/09/1969 | £4.00 | |
| West Ham United FC v Tottenham Hotspur FC 06/09/1969 | £5.00 | |
| Tottenham Hotspur FC v Manchester City FC 13/09/1969 | £4.00 |