| Tottenham Hotspur FC v Kaiserslautern 28/10/1999 | £5.00 | |
| Sunderland FC v Tottenham Hotspur FC 31/10/1999 | £6.50 | |
| Tottenham Hotspur FC v Arsenal FC 07/11/1999 | £5.00 | |
| Southampton FC v Tottenham Hotspur FC 20/11/1999 | £3.50 | |
| Southampton FC v Tottenham Hotspur FC 20/11/1999 | £2.00 | |
| Southampton FC v Tottenham Hotspur FC 20/11/1999 | £3.50 | |
| Fulham FC v Tottenham Hotspur FC 01/12/1999 | £4.50 | |
| 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 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 |