| Wimbledon v Barnsley FC 11/12/1999 | View match | |
| Bolton Wanderers FC v Wimbledon 14/12/1999 | View match | |
| Arsenal FC v Wimbledon 18/12/1999 | £3.00 | |
| Arsenal FC v Wimbledon 18/12/1999 | £6.50 | |
| Arsenal FC v Wimbledon 18/12/1999 | £4.00 | |
| 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 | |
| Wimbledon v Sunderland FC 03/01/2000 | View match | |
| Fulham FC v Wimbledon 08/01/2000 | £6.50 | |
| Coventry City FC v Wimbledon 15/01/2000 | View match |