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Table & Scores on 23/10/1999
| Home | Away | Pl | W | D | L | F | A | W | D | L | F | A | Pts | Leeds United | 11 | 4 | 1 | 1 | 10 | 5 | 4 | 0 | 1 | 11 | 7 | 25 | Arsenal | 12 | 5 | 0 | 1 | 13 | 5 | 3 | 1 | 2 | 7 | 7 | 25 | Manchester United | 12 | 4 | 2 | 0 | 19 | 6 | 3 | 1 | 2 | 9 | 13 | 24 | Sunderland | 11 | 4 | 2 | 0 | 8 | 2 | 3 | 0 | 2 | 12 | 7 | 23 | Tottenham Hotspur | 11 | 4 | 0 | 2 | 15 | 11 | 2 | 2 | 1 | 5 | 4 | 20 | Leicester City | 12 | 4 | 2 | 0 | 11 | 6 | 2 | 0 | 4 | 9 | 11 | 20 | Chelsea | 10 | 4 | 0 | 1 | 13 | 3 | 2 | 1 | 2 | 4 | 4 | 19 | Aston Villa | 12 | 3 | 3 | 0 | 8 | 3 | 2 | 0 | 4 | 5 | 9 | 18 | Everton | 11 | 3 | 2 | 0 | 11 | 3 | 2 | 0 | 4 | 6 | 11 | 17 | West Ham United | 9 | 4 | 0 | 0 | 6 | 2 | 1 | 1 | 3 | 5 | 6 | 16 | Liverpool | 11 | 2 | 0 | 3 | 5 | 5 | 2 | 3 | 1 | 7 | 6 | 15 | Middlesbrough | 11 | 3 | 0 | 3 | 6 | 7 | 2 | 0 | 3 | 7 | 8 | 15 | Coventry City | 12 | 3 | 0 | 3 | 11 | 8 | 0 | 4 | 2 | 5 | 7 | 13 | Southampton | 11 | 2 | 2 | 2 | 10 | 10 | 1 | 1 | 3 | 8 | 12 | 12 | Wimbledon | 12 | 1 | 3 | 2 | 9 | 10 | 1 | 3 | 2 | 9 | 16 | 12 | Bradford City | 11 | 1 | 2 | 2 | 5 | 10 | 2 | 0 | 4 | 4 | 7 | 11 | Watford | 11 | 2 | 0 | 3 | 5 | 6 | 1 | 0 | 5 | 2 | 9 | 9 | Derby County | 11 | 1 | 0 | 5 | 3 | 12 | 1 | 3 | 1 | 7 | 7 | 9 | Newcastle United | 11 | 2 | 1 | 2 | 14 | 7 | 0 | 0 | 6 | 7 | 20 | 7 | Sheffield Wednesday | 12 | 1 | 1 | 4 | 7 | 9 | 0 | 1 | 5 | 1 | 18 | 5 |
| Aston Villa 1 (1) Wimbledon 1 (1) | Dublin 35 Earle 26 | Attendance: 27,160 |
| Bradford City 3 (2) Leicester City 1 (1) | Blake 12, Mills 40, Redfearn 66 Impey 21 | Attendance: 17,655 |
| Chelsea 2 (1) Arsenal 3 (0) | Flo 38, Petrescu 52 Kanu 75, 83, 90 | Attendance: 34,958 |
| Sheffield Wednesday 0 (0) Coventry City 0 (0) | Attendance: 23,296 |
| Southampton 1 (1) Liverpool 1 (0) | Soltvedt 39 Camara 81 | Attendance: 15,241 |
| Tottenham Hotspur 3 (2) Manchester United 1 (1) | Iversen 37, Scholes 40 Og, Carr 71 Giggs 23 | Attendance: 36,072 |