| Wolverhampton Wanderers FC v Tottenham Hotspur FC 07/12/1968 | ||
| Tottenham Hotspur FC v Manchester City FC 14/12/1968 | £4.50 | |
| Tottenham Hotspur FC v Manchester City FC 14/12/1968 | £3.50 | |
| West Ham United FC v Tottenham Hotspur FC 16/12/1968 | View match | |
| Liverpool FC v Tottenham Hotspur FC 21/12/1968 | View match | |
| Walsall FC v Tottenham Hotspur FC 04/01/1969 | View match | |
| Stoke City FC v Tottenham Hotspur FC 11/01/1969 | £4.00 | |
| Tottenham Hotspur FC v Leeds United FC 18/01/1969 | £2.00 | |
| Tottenham Hotspur FC v Wolverhampton Wanderers FC 25/01/1969 | £2.50 | |
| Tottenham Hotspur FC v Wolverhampton Wanderers FC 25/01/1969 | £4.50 | |
| Tottenham Hotspur FC v Wolverhampton Wanderers FC 25/01/1969 | £3.00 | |
| Tottenham Hotspur FC v Wolverhampton Wanderers FC 25/01/1969 | £2.50 |