| 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 | £2.00 | |
| Tottenham Hotspur FC v Aston Villa FC 15/04/2000 | £4.50 | |
| Tottenham Hotspur FC v Aston Villa FC 15/04/2000 | £3.00 | |
| Leicester City FC v Tottenham Hotspur FC 19/04/2000 | £4.50 | |
| Tottenham Hotspur FC v Wimbledon 22/04/2000 | £5.00 | |
| Tottenham Hotspur FC v Derby County FC 29/04/2000 | £5.00 | |
| Manchester United FC v Tottenham Hotspur FC 06/05/2000 | £5.50 | |
| Manchester United FC v Tottenham Hotspur FC 06/05/2000 | £4.00 | |
| Tottenham Hotspur FC v Sunderland FC 14/05/2000 | £5.00 | |
| Fulham FC v Tottenham Hotspur FC 02/08/2000 | £6.50 |