| Tottenham Hotspur FC v Crewe Alexandra FC 13/10/1999 | £3.50 | |
| Tottenham Hotspur FC v Crewe Alexandra FC 13/10/1999 | £5.00 | |
| Derby County FC v Tottenham Hotspur FC 16/10/1999 | £4.00 | |
| Tottenham Hotspur FC v Manchester United FC 23/10/1999 | £5.00 | |
| Tottenham Hotspur FC v Kaiserslautern 28/10/1999 | £5.00 | |
| Sunderland FC v Tottenham Hotspur FC 31/10/1999 | £6.50 | |
| Kaiserslautern v Tottenham Hotspur FC 04/11/1999 | £18.99 | |
| Kaiserslautern v Tottenham Hotspur FC 04/11/1999 | £21.99 | |
| Tottenham Hotspur FC v Arsenal FC 07/11/1999 | £5.00 | |
| Southampton FC v Tottenham Hotspur FC 20/11/1999 | £2.00 | |
| Southampton FC v Tottenham Hotspur FC 20/11/1999 | £3.50 | |
| Southampton FC v Tottenham Hotspur FC 20/11/1999 | £3.50 |