| Charlton Athletic FC v Wimbledon 08/02/1999 | £3.00 | |
| Wimbledon v Tottenham Hotspur FC 16/02/1999 | £7.50 | |
| Wimbledon v Tottenham Hotspur FC 16/02/1999 | £5.50 | |
| Wimbledon v Chelsea FC 11/04/1999 | £4.50 | |
| Arsenal FC v Wimbledon 19/04/1999 | £3.50 | |
| Arsenal FC v Wimbledon 19/04/1999 | £2.00 | |
| Wimbledon v Tottenham Hotspur FC 26/09/1999 | £5.00 | |
| Sheffield Wednesday FC v Wimbledon 02/10/1999 | £4.00 | |
| Sheffield Wednesday FC v Wimbledon 02/10/1999 | £2.50 | |
| Aston Villa FC v Wimbledon 23/10/1999 | £3.00 | |
| Liverpool FC v Wimbledon 28/12/1999 | £5.00 | |
| Liverpool FC v Wimbledon 28/12/1999 | £4.00 |