| Tottenham Hotspur FC v Chelsea FC 10/05/1999 | £3.00 | |
| Tottenham Hotspur FC v Chelsea FC 10/05/1999 | £4.50 | |
| Tottenham Hotspur FC v Chelsea FC 10/05/1999 | £2.50 | |
| Manchester United FC v Tottenham Hotspur FC 16/05/1999 | £39.99 | |
| Heart Of Midlothian (Hearts) v Tottenham Hotspur FC 24/07/1999 | £6.50 | |
| Queens Park Rangers FC v Tottenham Hotspur FC 28/07/1999 | £7.50 | |
| Wolverhampton Wanderers FC v Tottenham Hotspur FC 31/07/1999 | £7.50 | |
| West Ham United FC v Tottenham Hotspur FC 07/08/1999 | £5.50 | |
| Tottenham Hotspur FC v Newcastle United FC 09/08/1999 | £5.50 | |
| Tottenham Hotspur FC v Everton FC 14/08/1999 | £5.00 | |
| Sheffield Wednesday FC v Tottenham Hotspur FC 21/08/1999 | £6.50 | |
| Sheffield Wednesday FC v Tottenham Hotspur FC 21/08/1999 | £4.00 |