| ROUND | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 |
| 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | 31 | 32 | 33 | 34 | 35 | 36 | 37 | 38 |
| Season archive |
| Games | Goals | H | D | A | ||||
| 46 | 125 | 2.71 | 20 | 43.48% | 8 | 17.39% | 18 | 39.13% |
| 1999/00 | Overall | Home | Away | |||||||||||||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | P | W | D | L | F | A | P | W | D | L | F | A | ||||
| 1 | Manchester United | 5 | 4 | 1 | 0 | 11 | 3 | +8 | 13 | WWWW | 2 | 2 | 0 | 0 | 6 | 0 | 3 | 2 | 1 | 0 | 5 | 3 | ||
| 2 | 3 | Aston Villa | 5 | 3 | 1 | 1 | 7 | 3 | +4 | 10 | WLXW | 2 | 1 | 1 | 0 | 5 | 2 | 3 | 2 | 0 | 1 | 2 | 1 | |
| 3 | 5 | Arsenal | 5 | 3 | 1 | 1 | 7 | 4 | +3 | 10 | WLOW | 3 | 2 | 0 | 1 | 5 | 3 | 2 | 1 | 1 | 0 | 2 | 1 | |
| 4 | 2 | Tottenham Hotspur | 4 | 3 | 0 | 1 | 8 | 5 | +3 | 9 | WWWL | 2 | 2 | 0 | 0 | 6 | 3 | 2 | 1 | 0 | 1 | 2 | 2 | |
| 5 | 2 | Middlesbrough | 5 | 3 | 0 | 2 | 7 | 7 | +0 | 9 | LWWW | 3 | 1 | 0 | 2 | 1 | 4 | 2 | 2 | 0 | 0 | 6 | 3 | |
| 6 | 2 | Chelsea | 3 | 2 | 1 | 0 | 7 | 2 | +5 | 7 | WXW- | 2 | 2 | 0 | 0 | 5 | 0 | 1 | 0 | 1 | 0 | 2 | 2 | |
| 7 | 7 | Everton | 5 | 2 | 1 | 2 | 11 | 8 | +3 | 7 | WWLL | 3 | 2 | 1 | 0 | 9 | 2 | 2 | 0 | 0 | 2 | 2 | 6 | |
| 8 | 7 | Leicester City | 5 | 2 | 1 | 2 | 8 | 6 | +2 | 7 | WLXW | 2 | 1 | 1 | 0 | 3 | 2 | 3 | 1 | 0 | 2 | 5 | 4 | |
| 9 | 3 | West Ham United | 3 | 2 | 1 | 0 | 5 | 3 | +2 | 7 | WXW- | 2 | 2 | 0 | 0 | 3 | 1 | 1 | 0 | 1 | 0 | 2 | 2 | |
| 10 | 3 | Leeds United | 5 | 2 | 1 | 2 | 6 | 5 | +1 | 7 | LWLW | 3 | 1 | 1 | 1 | 3 | 3 | 2 | 1 | 0 | 1 | 3 | 2 | |
| 11 | 5 | Sunderland | 5 | 2 | 1 | 2 | 5 | 7 | -2 | 7 | WLOW | 2 | 1 | 1 | 0 | 2 | 0 | 3 | 1 | 0 | 2 | 3 | 7 | |
| 12 | 5 | Liverpool | 4 | 2 | 0 | 2 | 4 | 4 | +0 | 6 | WLLW | 1 | 0 | 0 | 1 | 0 | 1 | 3 | 2 | 0 | 1 | 4 | 3 | |
| 13 | 4 | Watford | 5 | 2 | 0 | 3 | 4 | 6 | -2 | 6 | LWWL | 3 | 1 | 0 | 2 | 3 | 4 | 2 | 1 | 0 | 1 | 1 | 2 | |
| 14 | 4 | Southampton | 4 | 2 | 0 | 2 | 6 | 9 | -3 | 6 | LWLW | 2 | 1 | 0 | 1 | 4 | 5 | 2 | 1 | 0 | 1 | 2 | 4 | |
| 15 | 4 | Wimbledon | 5 | 1 | 2 | 2 | 9 | 13 | -4 | 5 | LXXL | 2 | 0 | 1 | 1 | 3 | 4 | 3 | 1 | 1 | 1 | 6 | 9 | |
| 16 | 4 | Coventry City | 5 | 1 | 1 | 3 | 4 | 5 | -1 | 4 | LWXL | 3 | 1 | 0 | 2 | 3 | 3 | 2 | 0 | 1 | 1 | 1 | 2 | |
| 17 | 4 | Bradford City | 4 | 1 | 1 | 2 | 2 | 4 | -2 | 4 | LLXW | 1 | 0 | 1 | 0 | 1 | 1 | 3 | 1 | 0 | 2 | 1 | 3 | |
| 18 | 1 | Derby County | 5 | 1 | 1 | 3 | 4 | 7 | -3 | 4 | WLLL | 2 | 0 | 0 | 2 | 2 | 5 | 3 | 1 | 1 | 1 | 2 | 2 | |
| 19 | 1 | Newcastle United | 5 | 0 | 1 | 4 | 7 | 13 | -6 | 1 | LXLL | 3 | 0 | 1 | 2 | 4 | 6 | 2 | 0 | 0 | 2 | 3 | 7 | |
| 20 | Sheffield Wednesday | 5 | 0 | 1 | 4 | 3 | 11 | -8 | 1 | LLXL | 3 | 0 | 0 | 3 | 2 | 6 | 2 | 0 | 1 | 1 | 1 | 5 | ||
| 5 | +1 | Dwight YORKE (Manchester United) |
| 4 | +2 | Emile HESKEY (Leicester City) |
| +1 | Kevin PHILLIPS (Sunderland, 2p) | |
| 3 | Dion DUBLIN (Aston Villa) | |
| Michael BRIDGES (Leeds United) | ||
| Hamilton RICARD (Middlesbrough, 2p) | ||
| +1 | David UNSWORTH (Everton, 2p) | |
| Carl CORT (Wimbledon) |
| Monday, 23 August 1999 | |||||
| 5 | Leeds United | 1-2 | Liverpool | ||
| 20(og) | Song | 45 | Camara | ||
| 55(og) | Radebe | ||||
| Tuesday, 24 August 1999 | |||||
| 5 | Middlesbrough | 0-3 | Leicester City | ||
| 35 | Heskey | ||||
| 38 | Cottee | ||||
| 83 | Heskey | ||||
| 5 | Watford | 0-1 | Aston Villa | ||
| 68 | Delaney | ||||
| Wednesday, 25 August 1999 | |||||
| 5 | Arsenal | 2-0 | Bradford City | ||
| 8 | Vieira | ||||
| 17(p) | Kanu | ||||
| 5 | Coventry City | 1-2 | Manchester United | ||
| 80 | Aloisi | 62 | Scholes | ||
| 75 | Yorke | ||||
| 5 | Everton | 4-0 | Wimbledon | ||
| 16 | Unsworth | ||||
| 46 | Barmby | ||||
| 50 | Jeffers | ||||
| 68 | Campbell | ||||
| 5 | Newcastle United | 1-2 | Sunderland | ||
| 27 | Dyer | 64 | Quinn | ||
| 74 | Phillips | ||||
| 5 | Sheffield Wednesday | 0-2 | Derby County | ||
| 54 | Delap | ||||
| 79 | Sturridge | ||||