| Chelsea FC v Tottenham Hotspur FC 19/12/1998 | £2.50 | |
| Coventry City FC v Tottenham Hotspur FC 26/12/1998 | £5.00 | |
| Tottenham Hotspur FC v Everton FC 28/12/1998 | £3.00 | |
| Tottenham Hotspur FC v Everton FC 28/12/1998 | £4.50 | |
| Tottenham Hotspur FC v Everton FC 28/12/1998 | £3.00 | |
| Tottenham Hotspur FC v Watford FC 02/01/1999 | £3.00 | |
| Tottenham Hotspur FC v Watford FC 02/01/1999 | £5.00 | |
| Sheffield Wednesday FC v Tottenham Hotspur FC 09/01/1999 | £4.50 | |
| Tottenham Hotspur FC v Wimbledon 16/01/1999 | £3.00 | |
| Tottenham Hotspur FC v Wimbledon 16/01/1999 | £2.50 | |
| Tottenham Hotspur FC v Wimbledon 16/01/1999 | £5.00 | |
| Wimbledon v Tottenham Hotspur FC 23/01/1999 | £5.00 |