| Blackburn Rovers FC v Tottenham Hotspur FC 30/01/1999 | £7.50 | |
| Tottenham Hotspur FC v Wimbledon 02/02/1999 | £2.00 | |
| Tottenham Hotspur FC v Wimbledon 02/02/1999 | £4.50 | |
| Tottenham Hotspur FC v Coventry City FC 06/02/1999 | £4.50 | |
| Tottenham Hotspur FC v Coventry City FC 06/02/1999 | £2.00 | |
| Leeds United FC v Tottenham Hotspur FC 13/02/1999 | £4.50 | |
| Wimbledon v Tottenham Hotspur FC 16/02/1999 | £5.50 | |
| Wimbledon v Tottenham Hotspur FC 16/02/1999 | £7.50 | |
| 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 |