| Luton Town FC v Tottenham Hotspur FC 02/12/1989 | £3.50 | |
| Tottenham Hotspur FC v Everton FC 09/12/1989 | £3.00 | |
| Barnet FC v Tottenham Hotspur FC 12/12/1989 | View match | |
| Manchester United FC v Tottenham Hotspur FC 16/12/1989 | £3.00 | |
| Manchester United FC v Tottenham Hotspur FC 16/12/1989 | £1.50 | |
| Tottenham Hotspur FC v Millwall FC 26/12/1989 | £4.50 | |
| Tottenham Hotspur FC v Millwall FC 26/12/1989 | £4.00 | |
| Tottenham Hotspur FC v Millwall FC 26/12/1989 | £3.00 | |
| Tottenham Hotspur FC v Nottingham Forest FC 30/12/1989 | View match | |
| Coventry City FC v Tottenham Hotspur FC 01/01/1990 | View match | |
| Tottenham Hotspur FC v Southampton FC 06/01/1990 | £5.00 | |
| Tottenham Hotspur FC v Southampton FC 06/01/1990 | £4.00 |