| Tottenham Hotspur FC v Southampton FC 19/02/1969 | £4.00 | |
| Tottenham Hotspur FC v Southampton FC 19/02/1969 | £5.00 | |
| Tottenham Hotspur FC v Wolverhampton Wanderers FC 22/02/1969 | £3.00 | |
| Tottenham Hotspur FC v Wolverhampton Wanderers FC 22/02/1969 | £2.50 | |
| Manchester City FC v Tottenham Hotspur FC 01/03/1969 | £5.00 | |
| Manchester City FC v Tottenham Hotspur FC 01/03/1969 | £6.50 | |
| Tottenham Hotspur FC v Everton FC 08/03/1969 | £2.50 | |
| Tottenham Hotspur FC v Everton FC 08/03/1969 | £3.50 | |
| Tottenham Hotspur FC v Everton FC 08/03/1969 | £1.50 | |
| Arsenal FC v Tottenham Hotspur FC 24/03/1969 | £9.99 | |
| Tottenham Hotspur FC v Coventry City FC 04/04/1969 | £3.00 | |
| Tottenham Hotspur FC v Coventry City FC 04/04/1969 | £3.00 |