| 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 | £4.00 | |
| Sheffield Wednesday FC v Tottenham Hotspur FC 21/08/1999 | £6.50 | |
| Tottenham Hotspur FC v Leeds United FC 28/08/1999 | £4.00 | |
| Tottenham Hotspur FC v Leeds United FC 28/08/1999 | £5.00 | |
| 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 | £4.00 | |
| Tottenham Hotspur FC v Coventry City FC 19/09/1999 | £5.00 | |
| Wimbledon v Tottenham Hotspur FC 26/09/1999 | £5.00 |