| Fulham FC v Tottenham Hotspur FC 01/12/1999 | £4.50 | |
| Tottenham Hotspur FC v West Ham United FC 06/12/1999 | £4.50 | |
| Tottenham Hotspur FC v West Ham United FC 06/12/1999 | £3.50 | |
| Tottenham Hotspur FC v Newcastle United FC 12/12/1999 | £5.00 | |
| Middlesbrough FC v Tottenham Hotspur FC 18/12/1999 | £4.50 | |
| Newcastle United FC v Tottenham Hotspur FC 22/12/1999 | £4.50 | |
| 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 | |
| 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 |