| Tottenham Hotspur FC v Southampton FC 11/03/2000 | £4.50 | |
| Arsenal FC v Tottenham Hotspur FC 19/03/2000 | £4.50 | |
| Arsenal FC v Tottenham Hotspur FC 19/03/2000 | £3.50 | |
| Watford FC v Tottenham Hotspur FC 25/03/2000 | £2.50 | |
| Tottenham Hotspur FC v Middlesbrough FC 03/04/2000 | £4.50 | |
| Tottenham Hotspur FC v Middlesbrough FC 03/04/2000 | £3.00 | |
| Liverpool FC v Tottenham Hotspur FC 09/04/2000 | £4.50 | |
| Tottenham Hotspur FC v Aston Villa FC 15/04/2000 | £3.00 | |
| Tottenham Hotspur FC v Aston Villa FC 15/04/2000 | £2.00 | |
| Tottenham Hotspur FC v Aston Villa FC 15/04/2000 | £4.50 | |
| Leicester City FC v Tottenham Hotspur FC 19/04/2000 | £4.50 | |
| Tottenham Hotspur FC v Wimbledon 22/04/2000 | £5.00 |