| Tottenham Hotspur FC v Sheffield Wednesday FC 22/01/2000 | £4.50 | |
| Tottenham Hotspur FC v Chelsea FC 05/02/2000 | £4.50 | |
| Tottenham Hotspur FC v Chelsea FC 05/02/2000 | £4.00 | |
| Tottenham Hotspur FC v Chelsea FC 05/02/2000 | £3.00 | |
| Tottenham Hotspur FC v Chelsea FC 05/02/2000 | £3.50 | |
| Leeds United FC v Tottenham Hotspur FC 12/02/2000 | £4.50 | |
| Coventry City FC v Tottenham Hotspur FC 26/02/2000 | £4.50 | |
| Tottenham Hotspur FC v Bradford City FC 04/03/2000 | £4.50 | |
| Tottenham Hotspur FC v Southampton FC 11/03/2000 | £4.50 | |
| Tottenham Hotspur FC v Southampton FC 11/03/2000 | £3.00 | |
| Arsenal FC v Tottenham Hotspur FC 19/03/2000 | £4.50 | |
| Arsenal FC v Tottenham Hotspur FC 19/03/2000 | £3.50 |