| 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 | |
| Tottenham Hotspur FC v Leeds United FC 28/08/1999 | £4.00 | |
| Tottenham Hotspur FC v Leeds United FC 28/08/1999 | £5.00 | |
| Bishops Stortford v Tottenham Hotspur FC 03/09/1999 | View match | |
| Bradford City FC v Tottenham Hotspur FC 12/09/1999 | £6.50 | |
| Tottenham Hotspur FC v Zimbru Chisinau 16/09/1999 | £4.00 | |
| Tottenham Hotspur FC v Zimbru Chisinau 16/09/1999 | £5.00 |