| Nottingham Forest FC v Tottenham Hotspur FC 17/04/1999 | £4.50 | |
| Charlton Athletic FC v Tottenham Hotspur FC 20/04/1999 | £4.00 | |
| Charlton Athletic FC v Tottenham Hotspur FC 20/04/1999 | £4.50 | |
| Tottenham Hotspur FC v West Ham United FC 24/04/1999 | £4.50 | |
| Tottenham Hotspur FC v West Ham United FC 24/04/1999 | £2.00 | |
| Liverpool FC v Tottenham Hotspur FC 01/05/1999 | £5.00 | |
| Liverpool FC v Tottenham Hotspur FC 01/05/1999 | £4.50 | |
| Tottenham Hotspur FC v Arsenal FC 05/05/1999 | £3.00 | |
| Tottenham Hotspur FC v Arsenal FC 05/05/1999 | £4.50 | |
| Tottenham Hotspur FC v Chelsea FC 10/05/1999 | £3.00 | |
| Tottenham Hotspur FC v Chelsea FC 10/05/1999 | £2.50 | |
| Tottenham Hotspur FC v Chelsea FC 10/05/1999 | £4.50 |