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Table & Scores on 14/08/1999
| Home | Away | Pl | W | D | L | F | A | W | D | L | F | A | Pts | Manchester United | 3 | 2 | 0 | 0 | 6 | 0 | 0 | 1 | 0 | 1 | 1 | 7 | Arsenal | 3 | 1 | 0 | 0 | 2 | 1 | 1 | 1 | 0 | 2 | 1 | 7 | Aston Villa | 2 | 1 | 0 | 0 | 3 | 0 | 1 | 0 | 0 | 1 | 0 | 6 | Tottenham Hotspur | 3 | 2 | 0 | 0 | 6 | 3 | 0 | 0 | 1 | 0 | 1 | 6 | Middlesbrough | 3 | 0 | 0 | 1 | 0 | 1 | 2 | 0 | 0 | 6 | 3 | 6 | Chelsea | 2 | 1 | 0 | 0 | 4 | 0 | 0 | 1 | 0 | 2 | 2 | 4 | Leeds United | 3 | 0 | 1 | 0 | 0 | 0 | 1 | 0 | 1 | 3 | 2 | 4 | Bradford City | 2 | 0 | 1 | 0 | 1 | 1 | 1 | 0 | 0 | 1 | 0 | 4 | Wimbledon | 3 | 0 | 1 | 1 | 3 | 4 | 1 | 0 | 0 | 3 | 2 | 4 | Leicester City | 3 | 1 | 1 | 0 | 3 | 2 | 0 | 0 | 1 | 1 | 2 | 4 | Sunderland | 3 | 1 | 1 | 0 | 2 | 0 | 0 | 0 | 1 | 0 | 4 | 4 | West Ham United | 1 | 1 | 0 | 0 | 1 | 0 | 0 | 0 | 0 | 0 | 0 | 3 | Liverpool | 2 | 0 | 0 | 1 | 0 | 1 | 1 | 0 | 0 | 2 | 1 | 3 | Watford | 3 | 0 | 0 | 1 | 2 | 3 | 1 | 0 | 1 | 1 | 2 | 3 | Southampton | 2 | 0 | 0 | 1 | 0 | 3 | 1 | 0 | 0 | 1 | 0 | 3 | Coventry City | 3 | 0 | 0 | 1 | 0 | 1 | 0 | 1 | 1 | 1 | 2 | 1 | Derby County | 3 | 0 | 0 | 2 | 2 | 5 | 0 | 1 | 0 | 0 | 0 | 1 | Everton | 3 | 0 | 1 | 0 | 1 | 1 | 0 | 0 | 2 | 2 | 6 | 1 | Sheffield Wednesday | 3 | 0 | 0 | 1 | 1 | 2 | 0 | 1 | 1 | 1 | 5 | 1 | Newcastle United | 2 | 0 | 0 | 1 | 0 | 1 | 0 | 0 | 1 | 1 | 3 | 0 |
| Bradford City 1 (0) Sheffield Wednesday 1 (1) | Beagrie 89 Pen Dreyer 39 Og | Attendance: 18,276 |
| Derby County 1 (1) Middlesbrough 3 (2) | Burton 41 Deane 9, Ziege 20, Ricard 66 Pen | Attendance: 24,045 |
| Leicester City 2 (1) Chelsea 2 (0) | Heskey 10, Izzet 90 Pen Wise 48, Sinclair 90 Og | Attendance: 21,068 |
| Liverpool 0 (0) Watford 1 (1) | Mooney 14 | Attendance: 44,174 |
| Manchester United 2 (0) Leeds United 0 (0) | Yorke 76, 80 | Attendance: 55,187 |
| Sunderland 0 (0) Arsenal 0 (0) | Attendance: 41,680 |
| Tottenham Hotspur 3 (1) Everton 2 (1) | Sherwood 34, Leonhardsen 82, Iversen 86 Unsworth 24 Pen, 77 Pen | Attendance: 34,539 |
| Wimbledon 1 (0) Coventry City 1 (0) | Cort 67 McAllister 90 Pen | Attendance: 10,635 |