| Tottenham Hotspur FC v Watford FC 26/12/1999 | £4.00 | |
| Tottenham Hotspur FC v Watford FC 26/12/1999 | £4.50 | |
| Aston Villa FC v Tottenham Hotspur FC 29/12/1999 | £4.50 | |
| Aston Villa FC v Tottenham Hotspur FC 29/12/1999 | £2.50 | |
| Tottenham Hotspur FC v Liverpool FC 03/01/2000 | £5.00 | |
| Chelsea FC v Tottenham Hotspur FC 12/01/2000 | £4.00 | |
| Everton FC v Tottenham Hotspur FC 15/01/2000 | £3.00 | |
| Everton FC v Tottenham Hotspur FC 15/01/2000 | £4.50 | |
| Tottenham Hotspur FC v Sheffield Wednesday FC 22/01/2000 | £3.50 | |
| 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 |