| Tottenham Hotspur FC v Everton FC 28/12/1998 | £3.00 | |
| Tottenham Hotspur FC v Watford FC 02/01/1999 | £5.00 | |
| Tottenham Hotspur FC v Watford FC 02/01/1999 | £3.00 | |
| 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 | £5.00 | |
| Tottenham Hotspur FC v Wimbledon 16/01/1999 | £2.50 | |
| Wimbledon v Tottenham Hotspur FC 23/01/1999 | £5.00 | |
| Wimbledon v Tottenham Hotspur FC 23/01/1999 | £3.50 | |
| Tottenham Hotspur FC v Wimbledon 27/01/1999 | £4.50 | |
| Tottenham Hotspur FC v Wimbledon 27/01/1999 | £6.50 | |
| Tottenham Hotspur FC v Wimbledon 27/01/1999 | £2.00 |