| Sunday 14 May 2000 | ||||
|---|---|---|---|---|
| 16:00 | Aston Villa | 0 - 1 | Man Utd | Villa Park |
| 16:00 | Bradford | 1 - 0 | Liverpool | Coral Windows Stadium |
| 16:00 | Chelsea | 4 - 0 | Derby | Stamford Bridge |
| 16:00 | Everton | 0 - 2 | Middlesbrough | Goodison Park |
| 16:00 | Newcastle | 4 - 2 | Arsenal | St James' Park |
| 16:00 | Sheffield Wed | 4 - 0 | Leicester | Hillsborough |
| 16:00 | Southampton | 2 - 0 | Wimbledon | The Dell |
| 16:00 | Tottenham | 3 - 1 | Sunderland | White Hart Lane |
| 16:00 | Watford | 1 - 0 | Coventry | Vicarage Road Stadium |
| 16:00 | West Ham | 0 - 0 | Leeds | Boleyn Ground |
| Tuesday 9 May 2000 | ||||
|---|---|---|---|---|
| 19:45 | Arsenal | 3 - 3 | Sheffield Wed | Highbury |
| Monday 8 May 2000 | ||||
|---|---|---|---|---|
| 20:00 | Leeds | 1 - 1 | Everton | Elland Road |
| Sunday 7 May 2000 | ||||
|---|---|---|---|---|
| 16:00 | Liverpool | 0 - 0 | Southampton | Anfield |
| Saturday 6 May 2000 | ||||
|---|---|---|---|---|
| 15:00 | Arsenal | 2 - 1 | Chelsea | Highbury |
| 15:00 | Coventry | 4 - 1 | Sheffield Wed | Highfield Road |
| 15:00 | Derby | 0 - 0 | Newcastle | Pride Park Stadium |
| 15:00 | Leicester | 3 - 0 | Bradford | Filbert Street |
| 15:00 | Middlesbrough | 1 - 1 | Watford | The Riverside Stadium |
| 15:00 | Wimbledon | 2 - 2 | Aston Villa | Selhurst Park |
| 15:00 | Sunderland | 1 - 0 | West Ham | Stadium of Light |
| 11:30 | Man Utd | 3 - 1 | Tottenham | Old Trafford |
| Wednesday 3 May 2000 | ||||
|---|---|---|---|---|
| 19:45 | Leeds | 3 - 1 | Watford | Elland Road |
| 19:45 | Liverpool | 0 - 2 | Leicester | Anfield |
| Tuesday 2 May 2000 | ||||
|---|---|---|---|---|
| 19:45 | Arsenal | 2 - 1 | West Ham | Highbury |
| 19:45 | Middlesbrough | 2 - 2 | Newcastle | The Riverside Stadium |
| Sunday 30 April 2000 | ||||
|---|---|---|---|---|
| 16:00 | Sheffield Wed | 0 - 3 | Leeds | Hillsborough |
| 15:00 | Bradford | 3 - 0 | Wimbledon | Coral Windows Stadium |
| Saturday 29 April 2000 | ||||
|---|---|---|---|---|
| 15:00 | Aston Villa | 1 - 1 | Sunderland | Villa Park |
| 15:00 | Chelsea | 2 - 0 | Liverpool | Stamford Bridge |
| 15:00 | Everton | 0 - 1 | Arsenal | Goodison Park |
| 15:00 | Newcastle | 2 - 0 | Coventry | St James' Park |
| 15:00 | Southampton | 1 - 2 | Leicester | The Dell |
| 15:00 | Tottenham | 1 - 1 | Derby | White Hart Lane |
| 15:00 | West Ham | 0 - 1 | Middlesbrough | Boleyn Ground |
| 11:30 | Watford | 2 - 3 | Man Utd | Vicarage Road Stadium |
| Monday 24 April 2000 | ||||
|---|---|---|---|---|
| 15:00 | Sunderland | 0 - 1 | Bradford | Stadium of Light |
| 13:00 | Derby | 2 - 0 | Southampton | Pride Park Stadium |
| 12:00 | Man Utd | 3 - 2 | Chelsea | Old Trafford |
| Sunday 23 April 2000 | ||||
|---|---|---|---|---|
| 15:00 | Newcastle | 2 - 2 | Leeds | St James' Park |
| 15:00 | Watford | 2 - 3 | Arsenal | Vicarage Road Stadium |
| Saturday 22 April 2000 | ||||
|---|---|---|---|---|
| 15:00 | Aston Villa | 2 - 2 | Leicester | Villa Park |
| 15:00 | Chelsea | 1 - 1 | Middlesbrough | Stamford Bridge |
| 15:00 | Sheffield Wed | 0 - 2 | Sunderland | Hillsborough |
| 15:00 | Southampton | 1 - 3 | Man Utd | The Dell |
| 15:00 | Tottenham | 2 - 0 | Wimbledon | White Hart Lane |
| 15:00 | West Ham | 5 - 0 | Coventry | Boleyn Ground |
| Friday 21 April 2000 | ||||
|---|---|---|---|---|
| 20:00 | Everton | 0 - 0 | Liverpool | Goodison Park |
| 16:00 | Bradford | 4 - 4 | Derby | Coral Windows Stadium |
| Wednesday 19 April 2000 | ||||
|---|---|---|---|---|
| 19:45 | Leicester | 0 - 1 | Tottenham | Filbert Street |
| Sunday 16 April 2000 | ||||
|---|---|---|---|---|
| 16:00 | Leeds | 0 - 4 | Arsenal | Elland Road |
| 13:00 | Wimbledon | 1 - 2 | Liverpool | Selhurst Park |
| Saturday 15 April 2000 | ||||
|---|---|---|---|---|
| 15:06 | Coventry | 2 - 1 | Middlesbrough | Highfield Road |
| 15:06 | Derby | 1 - 2 | West Ham | Pride Park Stadium |
| 15:06 | Everton | 4 - 0 | Bradford | Goodison Park |
| 15:06 | Man Utd | 4 - 0 | Sunderland | Old Trafford |
| 15:06 | Newcastle | 0 - 2 | Leicester | St James' Park |
| 15:06 | Sheffield Wed | 1 - 0 | Chelsea | Hillsborough |
| 15:06 | Southampton | 2 - 0 | Watford | The Dell |
| 15:06 | Tottenham | 2 - 4 | Aston Villa | White Hart Lane |
| Wednesday 12 April 2000 | ||||
|---|---|---|---|---|
| 19:45 | Chelsea | 2 - 1 | Coventry | Stamford Bridge |
| 19:45 | Wimbledon | 0 - 2 | Sheffield Wed | Selhurst Park |
| 19:45 | West Ham | 2 - 1 | Newcastle | Boleyn Ground |
| Monday 10 April 2000 | ||||
|---|---|---|---|---|
| 20:00 | Middlesbrough | 3 - 4 | Man Utd | The Riverside Stadium |
| Sunday 9 April 2000 | ||||
|---|---|---|---|---|
| 15:00 | Aston Villa | 1 - 0 | Leeds | Villa Park |
| 15:00 | Liverpool | 2 - 0 | Tottenham | Anfield |
| Saturday 8 April 2000 | ||||
|---|---|---|---|---|
| 15:00 | Bradford | 1 - 2 | Southampton | Coral Windows Stadium |
| 15:00 | Leicester | 1 - 1 | Everton | Filbert Street |
| 15:00 | Sunderland | 2 - 1 | Wimbledon | Stadium of Light |
| 15:00 | Watford | 0 - 0 | Derby | Vicarage Road Stadium |
| Wednesday 5 April 2000 | ||||
|---|---|---|---|---|
| 19:45 | Sheffield Wed | 0 - 1 | Aston Villa | Hillsborough |
| Monday 3 April 2000 | ||||
|---|---|---|---|---|
| 20:00 | Tottenham | 2 - 3 | Middlesbrough | White Hart Lane |
| Sunday 2 April 2000 | ||||
|---|---|---|---|---|
| 13:00 | Derby | 3 - 0 | Leicester | Pride Park Stadium |
| Saturday 1 April 2000 | ||||
|---|---|---|---|---|
| 15:00 | Coventry | 0 - 3 | Liverpool | Highfield Road |
| 15:00 | Everton | 4 - 2 | Watford | Goodison Park |
| 15:00 | Leeds | 0 - 1 | Chelsea | Elland Road |
| 15:00 | Man Utd | 7 - 1 | West Ham | Old Trafford |
| 15:00 | Wimbledon | 1 - 3 | Arsenal | Selhurst Park |
| 15:00 | Newcastle | 2 - 0 | Bradford | St James' Park |
| 15:00 | Southampton | 1 - 2 | Sunderland | The Dell |
| Sunday 26 March 2000 | ||||
|---|---|---|---|---|
| 16:00 | Arsenal | 3 - 0 | Coventry | Highbury |
| 16:00 | West Ham | 2 - 1 | Wimbledon | Boleyn Ground |
| 15:00 | Leicester | 2 - 1 | Leeds | Filbert Street |
| Saturday 25 March 2000 | ||||
|---|---|---|---|---|
| 15:00 | Aston Villa | 2 - 0 | Derby | Villa Park |
| 15:00 | Bradford | 0 - 4 | Man Utd | Coral Windows Stadium |
| 15:00 | Chelsea | 1 - 1 | Southampton | Stamford Bridge |
| 15:00 | Liverpool | 2 - 1 | Newcastle | Anfield |
| 15:00 | Middlesbrough | 1 - 0 | Sheffield Wed | The Riverside Stadium |
| 15:00 | Sunderland | 2 - 1 | Everton | Stadium of Light |
| 15:00 | Watford | 1 - 1 | Tottenham | Vicarage Road Stadium |
| Sunday 19 March 2000 | ||||
|---|---|---|---|---|
| 16:00 | Everton | 0 - 2 | Newcastle | Goodison Park |
| 15:00 | Arsenal | 2 - 1 | Tottenham | Highbury |
| 15:00 | Leeds | 4 - 1 | Wimbledon | Elland Road |
| Saturday 18 March 2000 | ||||
|---|---|---|---|---|
| 15:00 | Coventry | 4 - 0 | Bradford | Highfield Road |
| 15:00 | Derby | 0 - 2 | Liverpool | Pride Park Stadium |
| 15:00 | Leicester | 0 - 2 | Man Utd | Filbert Street |
| 15:00 | Southampton | 2 - 0 | Aston Villa | The Dell |
| 15:00 | Sunderland | 1 - 1 | Middlesbrough | Stadium of Light |
| 15:00 | Watford | 1 - 0 | Sheffield Wed | Vicarage Road Stadium |
| 15:00 | West Ham | 0 - 0 | Chelsea | Boleyn Ground |
| Wednesday 15 March 2000 | ||||
|---|---|---|---|---|
| 19:45 | Coventry | 1 - 0 | Everton | Highfield Road |
| 19:45 | Liverpool | 0 - 0 | Aston Villa | Anfield |
| Sunday 12 March 2000 | ||||
|---|---|---|---|---|
| 16:00 | Bradford | 1 - 2 | Leeds | Coral Windows Stadium |
| 15:00 | Middlesbrough | 2 - 1 | Arsenal | The Riverside Stadium |
| Saturday 11 March 2000 | ||||
|---|---|---|---|---|
| 15:00 | Aston Villa | 1 - 0 | Coventry | Villa Park |
| 15:00 | Chelsea | 1 - 1 | Everton | Stamford Bridge |
| 15:00 | Liverpool | 1 - 1 | Sunderland | Anfield |
| 15:00 | Man Utd | 3 - 1 | Derby | Old Trafford |
| 15:00 | Wimbledon | 2 - 1 | Leicester | Selhurst Park |
| 15:00 | Newcastle | 1 - 0 | Watford | St James' Park |
| 15:00 | Sheffield Wed | 3 - 1 | West Ham | Hillsborough |
| 15:00 | Tottenham | 7 - 2 | Southampton | White Hart Lane |
| Wednesday 8 March 2000 | ||||
|---|---|---|---|---|
| 19:45 | West Ham | 2 - 0 | Southampton | Boleyn Ground |
| Sunday 5 March 2000 | ||||
|---|---|---|---|---|
| 16:00 | Leicester | 5 - 2 | Sunderland | Filbert Street |
| 15:00 | Aston Villa | 1 - 1 | Arsenal | Villa Park |
| 15:00 | Leeds | 3 - 0 | Coventry | Elland Road |
| Saturday 4 March 2000 | ||||
|---|---|---|---|---|
| 15:00 | Derby | 4 - 0 | Wimbledon | Pride Park Stadium |
| 15:00 | Everton | 1 - 1 | Sheffield Wed | Goodison Park |
| 15:00 | Newcastle | 0 - 1 | Chelsea | St James' Park |
| 15:00 | Southampton | 1 - 1 | Middlesbrough | The Dell |
| 15:00 | Tottenham | 1 - 1 | Bradford | White Hart Lane |
| 15:00 | Watford | 1 - 2 | West Ham | Vicarage Road Stadium |
| 11:30 | Man Utd | 1 - 1 | Liverpool | Old Trafford |
| Saturday 26 February 2000 | ||||
|---|---|---|---|---|
| 15:00 | Arsenal | 3 - 1 | Southampton | Highbury |
| 15:00 | Bradford | 1 - 1 | Aston Villa | Coral Windows Stadium |
| 15:00 | Chelsea | 2 - 1 | Watford | Stamford Bridge |
| 15:00 | Coventry | 0 - 1 | Tottenham | Highfield Road |
| 15:00 | Middlesbrough | 0 - 0 | Leeds | The Riverside Stadium |
| 15:00 | Wimbledon | 2 - 2 | Man Utd | Selhurst Park |
| 15:00 | Sheffield Wed | 0 - 2 | Newcastle | Hillsborough |
| 15:00 | Sunderland | 1 - 1 | Derby | Stadium of Light |
| 15:00 | West Ham | 0 - 4 | Everton | Boleyn Ground |
| Sunday 20 February 2000 | ||||
|---|---|---|---|---|
| 11:30 | Leeds | 0 - 1 | Man Utd | Elland Road |
| Saturday 19 February 2000 | ||||
|---|---|---|---|---|
| 15:00 | Middlesbrough | 2 - 0 | Coventry | The Riverside Stadium |
| Monday 14 February 2000 | ||||
|---|---|---|---|---|
| 20:00 | Middlesbrough | 0 - 4 | Aston Villa | The Riverside Stadium |
| Sunday 13 February 2000 | ||||
|---|---|---|---|---|
| 16:00 | Arsenal | 0 - 1 | Liverpool | Highbury |
| Saturday 12 February 2000 | ||||
|---|---|---|---|---|
| 15:00 | Chelsea | 3 - 1 | Wimbledon | Stamford Bridge |
| 15:00 | Coventry | 3 - 2 | Sunderland | Highfield Road |
| 15:00 | Everton | 2 - 1 | Derby | Goodison Park |
| 15:00 | Leeds | 1 - 0 | Tottenham | Elland Road |
| 15:00 | Newcastle | 3 - 0 | Man Utd | St James' Park |
| 15:00 | Sheffield Wed | 0 - 1 | Southampton | Hillsborough |
| 15:00 | Watford | 1 - 1 | Leicester | Vicarage Road Stadium |
| 15:00 | West Ham | 5 - 4 | Bradford | Boleyn Ground |
| Sunday 6 February 2000 | ||||
|---|---|---|---|---|
| 16:00 | Wimbledon | 0 - 3 | Everton | Selhurst Park |
| Saturday 5 February 2000 | ||||
|---|---|---|---|---|
| 15:00 | Aston Villa | 4 - 0 | Watford | Villa Park |
| 15:00 | Bradford | 2 - 1 | Arsenal | Coral Windows Stadium |
| 15:00 | Derby | 3 - 3 | Sheffield Wed | Pride Park Stadium |
| 15:00 | Leicester | 2 - 1 | Middlesbrough | Filbert Street |
| 15:00 | Liverpool | 3 - 1 | Leeds | Anfield |
| 15:00 | Man Utd | 3 - 2 | Coventry | Old Trafford |
| 15:00 | Southampton | 2 - 1 | West Ham | The Dell |
| 15:00 | Sunderland | 2 - 2 | Newcastle | Stadium of Light |
| 15:00 | Tottenham | 0 - 1 | Chelsea | White Hart Lane |
| Wednesday 2 February 2000 | ||||
|---|---|---|---|---|
| 20:00 | Sheffield Wed | 0 - 1 | Man Utd | Hillsborough |
| Saturday 29 January 2000 | ||||
|---|---|---|---|---|
| 15:00 | Man Utd | 1 - 0 | Middlesbrough | Old Trafford |
| Monday 24 January 2000 | ||||
|---|---|---|---|---|
| 20:00 | Man Utd | 1 - 1 | Arsenal | Old Trafford |
| Sunday 23 January 2000 | ||||
|---|---|---|---|---|
| 16:00 | Sunderland | 1 - 2 | Leeds | Stadium of Light |
| Saturday 22 January 2000 | ||||
|---|---|---|---|---|
| 15:00 | Aston Villa | 0 - 0 | Chelsea | Villa Park |
| 15:00 | Bradford | 3 - 2 | Watford | Coral Windows Stadium |
| 15:00 | Derby | 0 - 0 | Coventry | Pride Park Stadium |
| 15:00 | Leicester | 1 - 3 | West Ham | Filbert Street |
| 15:00 | Liverpool | 0 - 0 | Middlesbrough | Anfield |
| 15:00 | Wimbledon | 2 - 0 | Newcastle | Selhurst Park |
| 15:00 | Southampton | 2 - 0 | Everton | The Dell |
| 15:00 | Tottenham | 0 - 1 | Sheffield Wed | White Hart Lane |
| Sunday 16 January 2000 | ||||
|---|---|---|---|---|
| 16:00 | Newcastle | 5 - 0 | Southampton | St James' Park |
| Saturday 15 January 2000 | ||||
|---|---|---|---|---|
| 15:00 | Arsenal | 4 - 1 | Sunderland | Highbury |
| 15:00 | Chelsea | 1 - 1 | Leicester | Stamford Bridge |
| 15:00 | Coventry | 2 - 0 | Wimbledon | Highfield Road |
| 15:00 | Everton | 2 - 2 | Tottenham | Goodison Park |
| 15:00 | Middlesbrough | 1 - 4 | Derby | The Riverside Stadium |
| 15:00 | Sheffield Wed | 2 - 0 | Bradford | Hillsborough |
| 15:00 | Watford | 2 - 3 | Liverpool | Vicarage Road Stadium |
| 15:00 | West Ham | 1 - 1 | Aston Villa | Boleyn Ground |
| Wednesday 12 January 2000 | ||||
|---|---|---|---|---|
| 19:45 | Chelsea | 1 - 0 | Tottenham | Stamford Bridge |
| Saturday 8 January 2000 | ||||
|---|---|---|---|---|
| 15:00 | Bradford | 1 - 1 | Chelsea | Coral Windows Stadium |
| Tuesday 4 January 2000 | ||||
|---|---|---|---|---|
| 20:00 | Coventry | 2 - 2 | Chelsea | Highfield Road |
| Monday 3 January 2000 | ||||
|---|---|---|---|---|
| 17:30 | Everton | 2 - 2 | Leicester | Goodison Park |
| 15:00 | Derby | 2 - 0 | Watford | Pride Park Stadium |
| 15:00 | Leeds | 1 - 2 | Aston Villa | Elland Road |
| 15:00 | Wimbledon | 1 - 0 | Sunderland | Selhurst Park |
| 15:00 | Newcastle | 2 - 2 | West Ham | St James' Park |
| 15:00 | Sheffield Wed | 1 - 1 | Arsenal | Hillsborough |
| 15:00 | Southampton | 1 - 0 | Bradford | The Dell |
| 15:00 | Tottenham | 1 - 0 | Liverpool | White Hart Lane |
| Wednesday 29 December 1999 | ||||
|---|---|---|---|---|
| 20:00 | Chelsea | 3 - 0 | Sheffield Wed | Stamford Bridge |
| 19:45 | Aston Villa | 1 - 1 | Tottenham | Villa Park |
| Tuesday 28 December 1999 | ||||
|---|---|---|---|---|
| 20:00 | Sunderland | 2 - 2 | Man Utd | Stadium of Light |
| 15:00 | Arsenal | 2 - 0 | Leeds | Highbury |
| 15:00 | Bradford | 0 - 0 | Everton | Coral Windows Stadium |
| 15:00 | Leicester | 1 - 2 | Newcastle | Filbert Street |
| 15:00 | Liverpool | 3 - 1 | Wimbledon | Anfield |
| 15:00 | Watford | 3 - 2 | Southampton | Vicarage Road Stadium |
| 15:00 | West Ham | 1 - 1 | Derby | Boleyn Ground |
| Sunday 26 December 1999 | ||||
|---|---|---|---|---|
| 17:30 | Coventry | 3 - 2 | Arsenal | Highfield Road |
| 15:00 | Derby | 0 - 2 | Aston Villa | Pride Park Stadium |
| 15:00 | Everton | 5 - 0 | Sunderland | Goodison Park |
| 15:00 | Leeds | 2 - 1 | Leicester | Elland Road |
| 15:00 | Man Utd | 4 - 0 | Bradford | Old Trafford |
| 15:00 | Newcastle | 2 - 2 | Liverpool | St James' Park |
| 15:00 | Sheffield Wed | 1 - 0 | Middlesbrough | Hillsborough |
| 12:00 | Wimbledon | 2 - 2 | West Ham | Selhurst Park |
| 12:00 | Southampton | 1 - 2 | Chelsea | The Dell |
| 12:00 | Tottenham | 4 - 0 | Watford | White Hart Lane |
| Sunday 19 December 1999 | ||||
|---|---|---|---|---|
| 16:00 | Chelsea | 0 - 2 | Leeds | Stamford Bridge |
| Saturday 18 December 1999 | ||||
|---|---|---|---|---|
| 15:00 | Arsenal | 1 - 1 | Wimbledon | Highbury |
| 15:00 | Aston Villa | 2 - 1 | Sheffield Wed | Villa Park |
| 15:00 | Bradford | 2 - 0 | Newcastle | Coral Windows Stadium |
| 15:00 | Leicester | 0 - 1 | Derby | Filbert Street |
| 15:00 | Liverpool | 2 - 0 | Coventry | Anfield |
| 15:00 | Middlesbrough | 2 - 1 | Tottenham | The Riverside Stadium |
| 15:00 | Sunderland | 2 - 0 | Southampton | Stadium of Light |
| 15:00 | Watford | 1 - 3 | Everton | Vicarage Road Stadium |
| 15:00 | West Ham | 2 - 4 | Man Utd | Boleyn Ground |
| Monday 6 December 1999 | ||||
|---|---|---|---|---|
| 20:00 | Tottenham | 0 - 0 | West Ham | White Hart Lane |
| Sunday 5 December 1999 | ||||
|---|---|---|---|---|
| 16:00 | Liverpool | 4 - 1 | Sheffield Wed | Anfield |
| 15:00 | Derby | 0 - 1 | Leeds | Pride Park Stadium |
| Saturday 4 December 1999 | ||||
|---|---|---|---|---|
| 15:00 | Aston Villa | 0 - 1 | Newcastle | Villa Park |
| 15:00 | Bradford | 1 - 1 | Middlesbrough | Coral Windows Stadium |
| 15:00 | Man Utd | 5 - 1 | Everton | Old Trafford |
| 15:00 | Wimbledon | 5 - 0 | Watford | Selhurst Park |
| 15:00 | Southampton | 0 - 0 | Coventry | The Dell |
| 15:00 | Sunderland | 4 - 1 | Chelsea | Stadium of Light |
| 11:30 | Leicester | 0 - 3 | Arsenal | Filbert Street |
| Sunday 28 November 1999 | ||||
|---|---|---|---|---|
| 16:00 | Arsenal | 2 - 1 | Derby | Highbury |
| 16:00 | Chelsea | 1 - 0 | Bradford | Stamford Bridge |
| 15:00 | Leeds | 1 - 0 | Southampton | Elland Road |
| 15:00 | Newcastle | 2 - 1 | Tottenham | St James' Park |
| Saturday 27 November 1999 | ||||
|---|---|---|---|---|
| 15:00 | Coventry | 0 - 1 | Leicester | Highfield Road |
| 15:00 | Everton | 0 - 0 | Aston Villa | Goodison Park |
| 15:00 | Middlesbrough | 0 - 0 | Wimbledon | The Riverside Stadium |
| 15:00 | Watford | 2 - 3 | Sunderland | Vicarage Road Stadium |
| 15:00 | West Ham | 1 - 0 | Liverpool | Boleyn Ground |
| Monday 22 November 1999 | ||||
|---|---|---|---|---|
| 20:00 | Coventry | 2 - 1 | Aston Villa | Highfield Road |
| Sunday 21 November 1999 | ||||
|---|---|---|---|---|
| 16:00 | West Ham | 4 - 3 | Sheffield Wed | Boleyn Ground |
| Saturday 20 November 1999 | ||||
|---|---|---|---|---|
| 15:00 | Arsenal | 5 - 1 | Middlesbrough | Highbury |
| 15:00 | Derby | 1 - 2 | Man Utd | Pride Park Stadium |
| 15:00 | Everton | 1 - 1 | Chelsea | Goodison Park |
| 15:00 | Leeds | 2 - 1 | Bradford | Elland Road |
| 15:00 | Leicester | 2 - 1 | Wimbledon | Filbert Street |
| 15:00 | Southampton | 0 - 1 | Tottenham | The Dell |
| 15:00 | Sunderland | 0 - 2 | Liverpool | Stadium of Light |
| 15:00 | Watford | 1 - 1 | Newcastle | Vicarage Road Stadium |
| Sunday 7 November 1999 | ||||
|---|---|---|---|---|
| 16:00 | Chelsea | 0 - 0 | West Ham | Stamford Bridge |
| 16:00 | Wimbledon | 2 - 0 | Leeds | Selhurst Park |
| 16:00 | Tottenham | 2 - 1 | Arsenal | White Hart Lane |
| 15:00 | Newcastle | 1 - 1 | Everton | St James' Park |
| Saturday 6 November 1999 | ||||
|---|---|---|---|---|
| 15:00 | Aston Villa | 0 - 1 | Southampton | Villa Park |
| 15:00 | Bradford | 1 - 1 | Coventry | Coral Windows Stadium |
| 15:00 | Liverpool | 2 - 0 | Derby | Anfield |
| 15:00 | Man Utd | 2 - 0 | Leicester | Old Trafford |
| 15:00 | Middlesbrough | 1 - 1 | Sunderland | The Riverside Stadium |
| 15:00 | Sheffield Wed | 2 - 2 | Watford | Hillsborough |
| Monday 1 November 1999 | ||||
|---|---|---|---|---|
| 20:00 | Liverpool | 3 - 1 | Bradford | Anfield |
| Sunday 31 October 1999 | ||||
|---|---|---|---|---|
| 16:00 | Coventry | 4 - 0 | Watford | Highfield Road |
| 15:00 | Sunderland | 2 - 1 | Tottenham | Stadium of Light |
| Saturday 30 October 1999 | ||||
|---|---|---|---|---|
| 15:00 | Arsenal | 0 - 0 | Newcastle | Highbury |
| 15:00 | Derby | 3 - 1 | Chelsea | Pride Park Stadium |
| 15:00 | Leeds | 1 - 0 | West Ham | Elland Road |
| 15:00 | Leicester | 3 - 0 | Sheffield Wed | Filbert Street |
| 15:00 | Man Utd | 3 - 0 | Aston Villa | Old Trafford |
| 15:00 | Middlesbrough | 2 - 1 | Everton | The Riverside Stadium |
| 15:00 | Wimbledon | 1 - 1 | Southampton | Selhurst Park |
| Wednesday 27 October 1999 | ||||
|---|---|---|---|---|
| 19:45 | Liverpool | 1 - 0 | West Ham | Anfield |
| Monday 25 October 1999 | ||||
|---|---|---|---|---|
| 20:00 | Newcastle | 2 - 0 | Derby | St James' Park |
| Sunday 24 October 1999 | ||||
|---|---|---|---|---|
| 16:00 | Watford | 1 - 3 | Middlesbrough | Vicarage Road Stadium |
| 15:00 | Everton | 4 - 4 | Leeds | Goodison Park |
| 15:00 | West Ham | 1 - 1 | Sunderland | Boleyn Ground |
| Saturday 23 October 1999 | ||||
|---|---|---|---|---|
| 15:00 | Aston Villa | 1 - 1 | Wimbledon | Villa Park |
| 15:00 | Bradford | 3 - 1 | Leicester | Coral Windows Stadium |
| 15:00 | Chelsea | 2 - 3 | Arsenal | Stamford Bridge |
| 15:00 | Sheffield Wed | 0 - 0 | Coventry | Hillsborough |
| 15:00 | Southampton | 1 - 1 | Liverpool | The Dell |
| 15:00 | Tottenham | 3 - 1 | Man Utd | White Hart Lane |
| Monday 18 October 1999 | ||||
|---|---|---|---|---|
| 20:00 | Sunderland | 2 - 1 | Aston Villa | Stadium of Light |
| Sunday 17 October 1999 | ||||
|---|---|---|---|---|
| 16:00 | Middlesbrough | 2 - 0 | West Ham | The Riverside Stadium |
| Saturday 16 October 1999 | ||||
|---|---|---|---|---|
| 15:00 | Arsenal | 4 - 1 | Everton | Highbury |
| 15:00 | Coventry | 4 - 1 | Newcastle | Highfield Road |
| 15:00 | Derby | 0 - 1 | Tottenham | Pride Park Stadium |
| 15:00 | Leeds | 2 - 0 | Sheffield Wed | Elland Road |
| 15:00 | Leicester | 2 - 1 | Southampton | Filbert Street |
| 15:00 | Liverpool | 1 - 0 | Chelsea | Anfield |
| 15:00 | Man Utd | 4 - 1 | Watford | Old Trafford |
| 15:00 | Wimbledon | 3 - 2 | Bradford | Selhurst Park |
| Monday 4 October 1999 | ||||
|---|---|---|---|---|
| 20:00 | Southampton | 3 - 3 | Derby | The Dell |
| Sunday 3 October 1999 | ||||
|---|---|---|---|---|
| 16:00 | Chelsea | 5 - 0 | Man Utd | Stamford Bridge |
| 16:00 | Tottenham | 2 - 3 | Leicester | White Hart Lane |
| 16:00 | West Ham | 2 - 1 | Arsenal | Boleyn Ground |
| 15:00 | Newcastle | 2 - 1 | Middlesbrough | St James' Park |
| 15:00 | Watford | 1 - 2 | Leeds | Vicarage Road Stadium |
| Saturday 2 October 1999 | ||||
|---|---|---|---|---|
| 15:00 | Aston Villa | 0 - 0 | Liverpool | Villa Park |
| 15:00 | Bradford | 0 - 4 | Sunderland | Coral Windows Stadium |
| 15:00 | Everton | 1 - 1 | Coventry | Goodison Park |
| 15:00 | Sheffield Wed | 5 - 1 | Wimbledon | Hillsborough |
| Monday 27 September 1999 | ||||
|---|---|---|---|---|
| 20:00 | Liverpool | 0 - 1 | Everton | Anfield |
| Sunday 26 September 1999 | ||||
|---|---|---|---|---|
| 16:00 | Wimbledon | 1 - 1 | Tottenham | Selhurst Park |
| Saturday 25 September 1999 | ||||
|---|---|---|---|---|
| 15:00 | Arsenal | 1 - 0 | Watford | Highbury |
| 15:00 | Coventry | 1 - 0 | West Ham | Highfield Road |
| 15:00 | Derby | 0 - 1 | Bradford | Pride Park Stadium |
| 15:00 | Leeds | 3 - 2 | Newcastle | Elland Road |
| 15:00 | Leicester | 3 - 1 | Aston Villa | Filbert Street |
| 15:00 | Man Utd | 3 - 3 | Southampton | Old Trafford |
| 15:00 | Middlesbrough | 0 - 1 | Chelsea | The Riverside Stadium |
| 15:00 | Sunderland | 1 - 0 | Sheffield Wed | Stadium of Light |
| Sunday 19 September 1999 | ||||
|---|---|---|---|---|
| 16:00 | Leeds | 2 - 0 | Middlesbrough | Elland Road |
| 15:00 | Everton | 1 - 0 | West Ham | Goodison Park |
| 15:00 | Newcastle | 8 - 0 | Sheffield Wed | St James' Park |
| 15:00 | Tottenham | 3 - 2 | Coventry | White Hart Lane |
| Saturday 18 September 1999 | ||||
|---|---|---|---|---|
| 15:00 | Aston Villa | 1 - 0 | Bradford | Villa Park |
| 15:00 | Derby | 0 - 5 | Sunderland | Pride Park Stadium |
| 15:00 | Leicester | 2 - 2 | Liverpool | Filbert Street |
| 15:00 | Man Utd | 1 - 1 | Wimbledon | Old Trafford |
| 15:00 | Southampton | 0 - 1 | Arsenal | The Dell |
| 15:00 | Watford | 1 - 0 | Chelsea | Vicarage Road Stadium |
| Sunday 12 September 1999 | ||||
|---|---|---|---|---|
| 16:00 | Bradford | 1 - 1 | Tottenham | Coral Windows Stadium |
| Saturday 11 September 1999 | ||||
|---|---|---|---|---|
| 15:00 | Arsenal | 3 - 1 | Aston Villa | Highbury |
| 15:00 | Chelsea | 1 - 0 | Newcastle | Stamford Bridge |
| 15:00 | Coventry | 3 - 4 | Leeds | Highfield Road |
| 15:00 | Middlesbrough | 3 - 2 | Southampton | The Riverside Stadium |
| 15:00 | Wimbledon | 2 - 2 | Derby | Selhurst Park |
| 15:00 | Sheffield Wed | 0 - 2 | Everton | Hillsborough |
| 15:00 | Sunderland | 2 - 0 | Leicester | Stadium of Light |
| 15:00 | West Ham | 1 - 0 | Watford | Boleyn Ground |
| 11:30 | Liverpool | 2 - 3 | Man Utd | Anfield |
| Monday 30 August 1999 | ||||
|---|---|---|---|---|
| 20:00 | Leicester | 1 - 0 | Watford | Filbert Street |
| 13:00 | Man Utd | 5 - 1 | Newcastle | Old Trafford |
| Sunday 29 August 1999 | ||||
|---|---|---|---|---|
| 16:00 | Sunderland | 1 - 1 | Coventry | Stadium of Light |
| Saturday 28 August 1999 | ||||
|---|---|---|---|---|
| 15:00 | Aston Villa | 1 - 0 | Middlesbrough | Villa Park |
| 15:00 | Bradford | 0 - 3 | West Ham | Coral Windows Stadium |
| 15:00 | Derby | 1 - 0 | Everton | Pride Park Stadium |
| 15:00 | Liverpool | 2 - 0 | Arsenal | Anfield |
| 15:00 | Wimbledon | 0 - 1 | Chelsea | Selhurst Park |
| 15:00 | Southampton | 2 - 0 | Sheffield Wed | The Dell |
| 15:00 | Tottenham | 1 - 2 | Leeds | White Hart Lane |
| Wednesday 25 August 1999 | ||||
|---|---|---|---|---|
| 20:00 | Everton | 4 - 0 | Wimbledon | Goodison Park |
| 19:45 | Arsenal | 2 - 0 | Bradford | Highbury |
| 19:45 | Coventry | 1 - 2 | Man Utd | Highfield Road |
| 19:45 | Newcastle | 1 - 2 | Sunderland | St James' Park |
| 19:45 | Sheffield Wed | 0 - 2 | Derby | Hillsborough |
| Tuesday 24 August 1999 | ||||
|---|---|---|---|---|
| 19:45 | Middlesbrough | 0 - 3 | Leicester | The Riverside Stadium |
| 19:45 | Watford | 0 - 1 | Aston Villa | Vicarage Road Stadium |
| Monday 23 August 1999 | ||||
|---|---|---|---|---|
| 20:00 | Leeds | 1 - 2 | Liverpool | Elland Road |
| Sunday 22 August 1999 | ||||
|---|---|---|---|---|
| 16:00 | Arsenal | 1 - 2 | Man Utd | Highbury |
| Saturday 21 August 1999 | ||||
|---|---|---|---|---|
| 15:00 | Chelsea | 1 - 0 | Aston Villa | Stamford Bridge |
| 15:00 | Coventry | 2 - 0 | Derby | Highfield Road |
| 15:00 | Everton | 4 - 1 | Southampton | Goodison Park |
| 15:00 | Leeds | 2 - 1 | Sunderland | Elland Road |
| 15:00 | Middlesbrough | 1 - 0 | Liverpool | The Riverside Stadium |
| 15:00 | Newcastle | 3 - 3 | Wimbledon | St James' Park |
| 15:00 | Sheffield Wed | 1 - 2 | Tottenham | Hillsborough |
| 15:00 | Watford | 1 - 0 | Bradford | Vicarage Road Stadium |
| 15:00 | West Ham | 2 - 1 | Leicester | Boleyn Ground |
| Monday 16 August 1999 | ||||
|---|---|---|---|---|
| 20:00 | Aston Villa | 2 - 2 | West Ham | Villa Park |
| Sunday 15 August 1999 | ||||
|---|---|---|---|---|
| 16:00 | Southampton | 4 - 2 | Newcastle | The Dell |
| Saturday 14 August 1999 | ||||
|---|---|---|---|---|
| 15:00 | Bradford | 1 - 1 | Sheffield Wed | Coral Windows Stadium |
| 15:00 | Derby | 1 - 3 | Middlesbrough | Pride Park Stadium |
| 15:00 | Leicester | 2 - 2 | Chelsea | Filbert Street |
| 15:00 | Liverpool | 0 - 1 | Watford | Anfield |
| 15:00 | Wimbledon | 1 - 1 | Coventry | Selhurst Park |
| 15:00 | Sunderland | 0 - 0 | Arsenal | Stadium of Light |
| 15:00 | Tottenham | 3 - 2 | Everton | White Hart Lane |
| 12:00 | Man Utd | 2 - 0 | Leeds | Old Trafford |
| Wednesday 11 August 1999 | ||||
|---|---|---|---|---|
| 20:00 | Man Utd | 4 - 0 | Sheffield Wed | Old Trafford |
| 19:45 | Aston Villa | 3 - 0 | Everton | Villa Park |
| 19:45 | Leicester | 1 - 0 | Coventry | Filbert Street |
| 19:45 | Southampton | 0 - 3 | Leeds | The Dell |
| Tuesday 10 August 1999 | ||||
|---|---|---|---|---|
| 20:00 | Derby | 1 - 2 | Arsenal | Pride Park Stadium |
| 19:45 | Wimbledon | 2 - 3 | Middlesbrough | Selhurst Park |
| 19:45 | Sunderland | 2 - 0 | Watford | Stadium of Light |
| Monday 9 August 1999 | ||||
|---|---|---|---|---|
| 20:00 | Tottenham | 3 - 1 | Newcastle | White Hart Lane |
| Sunday 8 August 1999 | ||||
|---|---|---|---|---|
| 16:00 | Everton | 1 - 1 | Man Utd | Goodison Park |
| Saturday 7 August 1999 | ||||
|---|---|---|---|---|
| 15:00 | Arsenal | 2 - 1 | Leicester | Highbury |
| 15:00 | Chelsea | 4 - 0 | Sunderland | Stamford Bridge |
| 15:00 | Coventry | 0 - 1 | Southampton | Highfield Road |
| 15:00 | Leeds | 0 - 0 | Derby | Elland Road |
| 15:00 | Middlesbrough | 0 - 1 | Bradford | The Riverside Stadium |
| 15:00 | Newcastle | 0 - 1 | Aston Villa | St James' Park |
| 15:00 | Sheffield Wed | 1 - 2 | Liverpool | Hillsborough |
| 15:00 | Watford | 2 - 3 | Wimbledon | Vicarage Road Stadium |
| 15:00 | West Ham | 1 - 0 | Tottenham | Boleyn Ground |
.