| Arsenal FC v Wimbledon 19/04/1999 | £5.00 | |
| Wimbledon v Tottenham Hotspur FC 26/09/1999 | £5.00 | |
| Sheffield Wednesday FC v Wimbledon 02/10/1999 | £2.50 | |
| Sheffield Wednesday FC v Wimbledon 02/10/1999 | £4.00 | |
| Aston Villa FC v Wimbledon 23/10/1999 | £3.00 | |
| Arsenal FC v Wimbledon 18/12/1999 | £5.00 | |
| Wimbledon v West Ham United FC 26/12/1999 | £6.50 | |
| Liverpool FC v Wimbledon 28/12/1999 | £4.00 | |
| Liverpool FC v Wimbledon 28/12/1999 | £5.00 | |
| Fulham FC v Wimbledon 08/01/2000 | £6.50 | |
| Chelsea FC v Wimbledon 12/02/2000 | £3.00 | |
| West Ham United FC v Wimbledon 26/03/2000 | £6.00 |