| A(D) | Clubs | VS | MD | |
|---|---|---|---|---|
| 23(139) | Leeds United | Aston Villa | 03-Jan-2000 | Match Details |
| 24(306) | Liverpool | Leicester City | 18-Sep-1999 | Match Details |
| 24(94) | Watford | Leeds United | 03-May-2000 | Match Details |
| 25(45) | Aston Villa | Sheffield Wednesday | 05-Apr-2000 | Match Details |
| 25(74) | Tottenham Hotspur | Manchester United | 06-May-2000 | Match Details |
| 25(114) | Milton Keynes Dons | Sunderland | 03-Jan-2000 | Match Details |
| 25(165) | Derby County | Middlesbrough | 15-Jan-2000 | Match Details |
| 25(169) | Coventry City | Derby County | 22-Jan-2000 | Match Details |
| 26(221) | Newcastle United | Sunderland | 25-Aug-1999 | Match Details |
| 26(245) | Leicester City | West Ham United | 22-Jan-2000 | Match Details |
| 26(269) | Manchester United | Leicester City | 06-Nov-1999 | Match Details |
| 26(296) | Arsenal | Manchester United | 22-Aug-1999 | Match Details |
| 26(364) | Sunderland | Liverpool | 11-Mar-2000 | Match Details |
| 26(40) | West Ham United | Newcastle United | 03-Jan-2000 | Match Details |
| 26(52) | Southampton | Everton | 22-Jan-2000 | Match Details |
| 26(140) | Sheffield Wednesday | Southampton | 28-Aug-1999 | Match Details |
| 27(261) | Everton | Middlesbrough | 14-May-2000 | Match Details |
| 28(275) | Middlesbrough | Bradford City | 07-Aug-1999 | Match Details |
| 28(72) | Chelsea | Everton | 20-Nov-1999 | Match Details |
| 29(3) | Bradford City | Middlesbrough | 04-Dec-1999 | Match Details |
MD = Match date,
A(D) = Age(Days).