| League | Date | Home Team | Score | Away Team |
|---|---|---|---|---|
| PL | 14-05-2000 | Southampton | 2 - 0 | Wimbledon |
| PL | 06-05-2000 | Wimbledon | 2 - 2 | Aston Villa |
| PL | 30-04-2000 | Bradford | 3 - 0 | Wimbledon |
| PL | 22-04-2000 | Tottenham | 2 - 0 | Wimbledon |
| PL | 16-04-2000 | Wimbledon | 1 - 2 | Liverpool |
| PL | 12-04-2000 | Wimbledon | 0 - 2 | Sheffield Weds |
| PL | 08-04-2000 | Sunderland | 2 - 1 | Wimbledon |
| PL | 01-04-2000 | Wimbledon | 1 - 3 | Arsenal |
| PL | 26-03-2000 | West Ham | 2 - 1 | Wimbledon |
| PL | 19-03-2000 | Leeds | 4 - 1 | Wimbledon |
| PL | 11-03-2000 | Wimbledon | 2 - 1 | Leicester |
| PL | 04-03-2000 | Derby | 4 - 0 | Wimbledon |
| PL | 26-02-2000 | Wimbledon | 2 - 2 | Man United |
| PL | 12-02-2000 | Chelsea | 3 - 1 | Wimbledon |
| PL | 06-02-2000 | Wimbledon | 0 - 3 | Everton |
| PL | 22-01-2000 | Wimbledon | 2 - 0 | Newcastle |
| PL | 15-01-2000 | Coventry | 2 - 0 | Wimbledon |
| PL | 03-01-2000 | Wimbledon | 1 - 0 | Sunderland |
| PL | 28-12-1999 | Liverpool | 3 - 1 | Wimbledon |
| PL | 26-12-1999 | Wimbledon | 2 - 2 | West Ham |
| PL | 18-12-1999 | Arsenal | 1 - 1 | Wimbledon |
| PL | 04-12-1999 | Wimbledon | 5 - 0 | Watford |
| PL | 27-11-1999 | Middlesbrough | 0 - 0 | Wimbledon |
| PL | 20-11-1999 | Leicester | 2 - 1 | Wimbledon |
| PL | 07-11-1999 | Wimbledon | 2 - 0 | Leeds |
| PL | 30-10-1999 | Wimbledon | 1 - 1 | Southampton |
| PL | 23-10-1999 | Aston Villa | 1 - 1 | Wimbledon |
| PL | 16-10-1999 | Wimbledon | 3 - 2 | Bradford |
| PL | 02-10-1999 | Sheffield Weds | 5 - 1 | Wimbledon |
| PL | 26-09-1999 | Wimbledon | 1 - 1 | Tottenham |
| PL | 18-09-1999 | Man United | 1 - 1 | Wimbledon |
| PL | 11-09-1999 | Wimbledon | 2 - 2 | Derby |
| PL | 28-08-1999 | Wimbledon | 0 - 1 | Chelsea |
| PL | 25-08-1999 | Everton | 4 - 0 | Wimbledon |
| PL | 21-08-1999 | Newcastle | 3 - 3 | Wimbledon |
| PL | 14-08-1999 | Wimbledon | 1 - 1 | Coventry |
| PL | 10-08-1999 | Wimbledon | 2 - 3 | Middlesbrough |
| PL | 07-08-1999 | Watford | 2 - 3 | Wimbledon |