| Tottenham Hotspur FC v Middlesbrough FC 13/09/1998 | £2.00 | |
| Brentford FC v Tottenham Hotspur FC 15/09/1998 | £16.99 | |
| Southampton FC v Tottenham Hotspur FC 19/09/1998 | £3.50 | |
| Southampton FC v Tottenham Hotspur FC 19/09/1998 | £4.50 | |
| Tottenham Hotspur FC v Brentford FC 23/09/1998 | £3.50 | |
| Tottenham Hotspur FC v Brentford FC 23/09/1998 | £4.00 | |
| Tottenham Hotspur FC v Brentford FC 23/09/1998 | £4.50 | |
| Tottenham Hotspur FC v Leeds United FC 26/09/1998 | £2.00 | |
| Tottenham Hotspur FC v Leeds United FC 26/09/1998 | £4.50 | |
| Derby County FC v Tottenham Hotspur FC 03/10/1998 | £4.50 | |
| Leicester City FC v Tottenham Hotspur FC 19/10/1998 | £5.00 | |
| Tottenham Hotspur FC v Newcastle United FC 24/10/1998 | £1.50 |