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Table & Scores on 21/08/1999
| Home | Away | Pl | W | D | L | F | A | W | D | L | F | A | Pts | Tottenham Hotspur | 4 | 2 | 0 | 0 | 6 | 3 | 1 | 0 | 1 | 2 | 2 | 9 | Middlesbrough | 4 | 1 | 0 | 1 | 1 | 1 | 2 | 0 | 0 | 6 | 3 | 9 | Manchester United | 3 | 2 | 0 | 0 | 6 | 0 | 0 | 1 | 0 | 1 | 1 | 7 | Chelsea | 3 | 2 | 0 | 0 | 5 | 0 | 0 | 1 | 0 | 2 | 2 | 7 | Aston Villa | 4 | 1 | 1 | 0 | 5 | 2 | 1 | 0 | 1 | 1 | 1 | 7 | West Ham United | 3 | 2 | 0 | 0 | 3 | 1 | 0 | 1 | 0 | 2 | 2 | 7 | Leeds United | 4 | 1 | 1 | 0 | 2 | 1 | 1 | 0 | 1 | 3 | 2 | 7 | Arsenal | 3 | 1 | 0 | 0 | 2 | 1 | 1 | 1 | 0 | 2 | 1 | 7 | Watford | 4 | 1 | 0 | 1 | 3 | 3 | 1 | 0 | 1 | 1 | 2 | 6 | Southampton | 4 | 1 | 0 | 1 | 4 | 5 | 1 | 0 | 1 | 2 | 4 | 6 | Wimbledon | 4 | 0 | 1 | 1 | 3 | 4 | 1 | 1 | 0 | 6 | 5 | 5 | Coventry City | 4 | 1 | 0 | 1 | 2 | 1 | 0 | 1 | 1 | 1 | 2 | 4 | Bradford City | 3 | 0 | 1 | 0 | 1 | 1 | 1 | 0 | 1 | 1 | 1 | 4 | Everton | 4 | 1 | 1 | 0 | 5 | 2 | 0 | 0 | 2 | 2 | 6 | 4 | Leicester City | 4 | 1 | 1 | 0 | 3 | 2 | 0 | 0 | 2 | 2 | 4 | 4 | Sunderland | 4 | 1 | 1 | 0 | 2 | 0 | 0 | 0 | 2 | 1 | 6 | 4 | Liverpool | 3 | 0 | 0 | 1 | 0 | 1 | 1 | 0 | 1 | 2 | 2 | 3 | Newcastle United | 4 | 0 | 1 | 1 | 3 | 4 | 0 | 0 | 2 | 3 | 7 | 1 | Derby County | 4 | 0 | 0 | 2 | 2 | 5 | 0 | 1 | 1 | 0 | 2 | 1 | Sheffield Wednesday | 4 | 0 | 0 | 2 | 2 | 4 | 0 | 1 | 1 | 1 | 5 | 1 |
| Chelsea 1 (0) Aston Villa 0 (0) | Ehiogu 52 Og | Attendance: 35,071 |
| Coventry City 2 (1) Derby County 0 (0) | Keane 43, 67 | Attendance: 17,658 |
| Everton 4 (1) Southampton 1 (0) | Gough 36, Lundekvam 47 Og, Jeffers 48 Pahars 70 | Campbell 54 | Attendance: 31,755 |
| Leeds United 2 (0) Sunderland 1 (1) | Bowyer 52, Mills 71 Phillips 37 Pen | Attendance: 39,064 |
| Middlesbrough 1 (0) Liverpool 0 (0) | Deane 49 | Attendance: 34,783 |
| Newcastle United 3 (2) Wimbledon 3 (1) | Speed 7, Domi 28, Solano 46 Pen Hughes 44, Ainsworth 68, 90 | Attendance: 35,809 |
| Sheffield Wednesday 1 (1) Tottenham Hotspur 2 (2) | Carbone 23 Pen Ferdinand 19, Leonhardsen 41 | Attendance: 24,027 |
| Watford 1 (0) Bradford City 0 (0) | Mooney 71 | Attendance: 15,564 |
| West Ham United 2 (1) Leicester City 1 (1) | Wanchope 29, Di Canio 53 Heskey 2 | Attendance: 23,631 |