| 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 | |
| Tottenham Hotspur FC v Coventry City FC 19/09/1999 | £5.00 | |
| Tottenham Hotspur FC v Coventry City FC 19/09/1999 | £4.00 | |
| Wimbledon v Tottenham Hotspur FC 26/09/1999 | £5.00 | |
| Zimbru Chisinau v Tottenham Hotspur FC 30/09/1999 | View match | |
| Zimbru Chisinau v Tottenham Hotspur FC 30/09/1999 | £15.00 | |
| Zimbru Chisinau v Tottenham Hotspur FC 30/09/1999 | £6.50 | |
| Zimbru Chisinau v Tottenham Hotspur FC 30/09/1999 | £7.50 | |
| Tottenham Hotspur FC v Leicester City FC 03/10/1999 | £5.50 |