| Barnsley FC v Tottenham Hotspur FC 16/03/1999 | £6.50 | |
| Leicester City FC v Tottenham Hotspur FC 21/03/1999 | £10.00 | |
| Leicester City FC v Tottenham Hotspur FC 21/03/1999 | £12.50 | |
| Tottenham Hotspur FC v Leicester City FC 03/04/1999 | £4.50 | |
| Tottenham Hotspur FC v Leicester City FC 03/04/1999 | £3.00 | |
| Newcastle United FC v Tottenham Hotspur FC 05/04/1999 | £6.50 | |
| Newcastle United FC v Tottenham Hotspur FC 11/04/1999 | £7.50 | |
| 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 |