| Date | Result | OPP | FS | Home/Away |
|---|---|---|---|---|
| 07-Aug-1999 | lose |  Liverpool | 1-2 | home |
| 11-Aug-1999 | lose |  Manchester United | 4-0 | away |
| 21-Aug-1999 | lose |  Tottenham Hotspur | 1-2 | home |
| 25-Aug-1999 | lose |  Derby County | 0-2 | home |
| 28-Aug-1999 | lose |  Southampton | 2-0 | away |
| 11-Sep-1999 | lose |  Everton | 0-2 | home |
| 19-Sep-1999 | lose |  Newcastle United | 8-0 | away |
| 25-Sep-1999 | lose |  Sunderland | 1-0 | away |
| 16-Oct-1999 | lose |  Leeds United | 2-0 | away |
| 30-Oct-1999 | lose |  Leicester City | 3-0 | away |
| 06-Nov-1999 | draw |  Watford | 2-2 | home |
| 21-Nov-1999 | lose |  West Ham United | 4-3 | away |
| 29-Dec-1999 | lose |  Chelsea | 3-0 | away |
| 03-Jan-2000 | draw |  Arsenal | 1-1 | home |
| 02-Feb-2000 | lose | Manchester United | 0-1 | home |
| 12-Feb-2000 | lose | Southampton | 0-1 | home |
| 26-Feb-2000 | lose | Newcastle United | 0-2 | home |
| 04-Mar-2000 | draw | Everton | 1-1 | away |
| 11-Mar-2000 | win | West Ham United | 3-1 | home |
| 18-Mar-2000 | lose | Watford | 1-0 | away |
| 25-Mar-2000 | lose |  Middlesbrough | 1-0 | away |
| 05-Apr-2000 | lose |  Aston Villa | 0-1 | home |
| 22-Apr-2000 | lose | Sunderland | 0-2 | home |
| 30-Apr-2000 | lose | Leeds United | 0-3 | home |
| 06-May-2000 | lose |  Coventry City | 4-1 | away |
| 09-May-2000 | draw | Arsenal | 3-3 | away |
Overall ( 1 wins,4 draw,21 lost )
Home ( 1 wins,2 draw,10 lost )
Away ( 0 wins,2 draw,11 lost )
OPP = Opposition,
FS = Final score.