| Middlesbrough FC v Tottenham Hotspur FC 20/02/1999 | £5.00 | |
| Tottenham Hotspur FC v Leeds United FC 24/02/1999 | £6.50 | |
| Tottenham Hotspur FC v Derby County FC 27/02/1999 | £2.00 | |
| Tottenham Hotspur FC v Derby County FC 27/02/1999 | £4.50 | |
| Tottenham Hotspur FC v Southampton FC 02/03/1999 | £2.00 | |
| Tottenham Hotspur FC v Southampton FC 02/03/1999 | £4.50 | |
| Leeds United FC v Tottenham Hotspur FC 10/03/1999 | £5.00 | |
| Tottenham Hotspur FC v Aston Villa FC 13/03/1999 | £2.00 | |
| Tottenham Hotspur FC v Aston Villa FC 13/03/1999 | £4.50 | |
| Barnsley FC v Tottenham Hotspur FC 16/03/1999 | £6.50 | |
| Leicester City FC v Tottenham Hotspur FC 21/03/1999 | £10.00 | |
| Leicester City FC v Tottenham Hotspur FC 21/03/1999 | £12.50 |