| 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 | ||||
| 38 | 104 | 2.73 | 18 | 47.37% | 8 | 21.05% | 12 | 31.58% |
| 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 | 4 | 3 | 1 | 0 | 9 | 2 | +7 | 10 | WWWX | 2 | 2 | 0 | 0 | 6 | 0 | 2 | 1 | 1 | 0 | 3 | 2 | ||
| 2 | 2 | Tottenham Hotspur | 4 | 3 | 0 | 1 | 8 | 5 | +3 | 9 | WWWL | 2 | 2 | 0 | 0 | 6 | 3 | 2 | 1 | 0 | 1 | 2 | 2 | |
| 3 | 2 | Middlesbrough | 4 | 3 | 0 | 1 | 7 | 4 | +3 | 9 | WWWL | 2 | 1 | 0 | 1 | 1 | 1 | 2 | 2 | 0 | 0 | 6 | 3 | |
| 4 | 3 | Chelsea | 3 | 2 | 1 | 0 | 7 | 2 | +5 | 7 | WXW- | 2 | 2 | 0 | 0 | 5 | 0 | 1 | 0 | 1 | 0 | 2 | 2 | |
| 5 | 3 | Aston Villa | 4 | 2 | 1 | 1 | 6 | 3 | +3 | 7 | LXWW | 2 | 1 | 1 | 0 | 5 | 2 | 2 | 1 | 0 | 1 | 1 | 1 | |
| 6 | 2 | West Ham United | 3 | 2 | 1 | 0 | 5 | 3 | +2 | 7 | WXW- | 2 | 2 | 0 | 0 | 3 | 1 | 1 | 0 | 1 | 0 | 2 | 2 | |
| 7 | 2 | Leeds United | 4 | 2 | 1 | 1 | 5 | 3 | +2 | 7 | WLWO | 2 | 1 | 1 | 0 | 2 | 1 | 2 | 1 | 0 | 1 | 3 | 2 | |
| 8 | 5 | Arsenal | 4 | 2 | 1 | 1 | 5 | 4 | +1 | 7 | LOWW | 2 | 1 | 0 | 1 | 3 | 3 | 2 | 1 | 1 | 0 | 2 | 1 | |
| 9 | 6 | Watford | 4 | 2 | 0 | 2 | 4 | 5 | -1 | 6 | WWLL | 2 | 1 | 0 | 1 | 3 | 3 | 2 | 1 | 0 | 1 | 1 | 2 | |
| 10 | 4 | Southampton | 4 | 2 | 0 | 2 | 6 | 9 | -3 | 6 | LWLW | 2 | 1 | 0 | 1 | 4 | 5 | 2 | 1 | 0 | 1 | 2 | 4 | |
| 11 | Wimbledon | 4 | 1 | 2 | 1 | 9 | 9 | +0 | 5 | XXLW | 2 | 0 | 1 | 1 | 3 | 4 | 2 | 1 | 1 | 0 | 6 | 5 | ||
| 12 | 4 | Coventry City | 4 | 1 | 1 | 2 | 3 | 3 | +0 | 4 | WXLL | 2 | 1 | 0 | 1 | 2 | 1 | 2 | 0 | 1 | 1 | 1 | 2 | |
| 13 | 3 | Bradford City | 3 | 1 | 1 | 1 | 2 | 2 | +0 | 4 | LXW- | 1 | 0 | 1 | 0 | 1 | 1 | 2 | 1 | 0 | 1 | 1 | 1 | |
| 14 | 4 | Everton | 4 | 1 | 1 | 2 | 7 | 8 | -1 | 4 | WLLX | 2 | 1 | 1 | 0 | 5 | 2 | 2 | 0 | 0 | 2 | 2 | 6 | |
| 15 | 3 | Leicester City | 4 | 1 | 1 | 2 | 5 | 6 | -1 | 4 | LXWL | 2 | 1 | 1 | 0 | 3 | 2 | 2 | 0 | 0 | 2 | 2 | 4 | |
| 16 | 3 | Sunderland | 4 | 1 | 1 | 2 | 3 | 6 | -3 | 4 | LOWL | 2 | 1 | 1 | 0 | 2 | 0 | 2 | 0 | 0 | 2 | 1 | 6 | |
| 17 | 3 | Liverpool | 3 | 1 | 0 | 2 | 2 | 3 | -1 | 3 | LLW- | 1 | 0 | 0 | 1 | 0 | 1 | 2 | 1 | 0 | 1 | 2 | 2 | |
| 18 | 2 | Newcastle United | 4 | 0 | 1 | 3 | 6 | 11 | -5 | 1 | XLLL | 2 | 0 | 1 | 1 | 3 | 4 | 2 | 0 | 0 | 2 | 3 | 7 | |
| 19 | 2 | Derby County | 4 | 0 | 1 | 3 | 2 | 7 | -5 | 1 | LLLO | 2 | 0 | 0 | 2 | 2 | 5 | 2 | 0 | 1 | 1 | 0 | 2 | |
| 20 | 1 | Sheffield Wednesday | 4 | 0 | 1 | 3 | 3 | 9 | -6 | 1 | LXLL | 2 | 0 | 0 | 2 | 2 | 4 | 2 | 0 | 1 | 1 | 1 | 5 | |
| 4 | Dwight YORKE (Manchester United) | |
| 3 | Dion DUBLIN (Aston Villa) | |
| Michael BRIDGES (Leeds United) | ||
| Hamilton RICARD (Middlesbrough, 2p) | ||
| Carl CORT (Wimbledon) | ||
| +1 | Kevin PHILLIPS (Sunderland, 2p) | |
| 2 | +1 | Benito CARBONE (Sheffield Wednesday, 1p) |
| Tim SHERWOOD (Tottenham Hotspur) | ||
| +1 | Nolberto SOLANO (Newcastle United, 1p) | |
| +1 | Brian DEANE (Middlesbrough) | |
| +2 | Gareth AINSWORTH (Wimbledon) | |
| Hassan KACHLOUL (Southampton) | ||
| David UNSWORTH (Everton, 2p) | ||
| Muzzy IZZET (Leicester City, 2p) | ||
| Dennis BERGKAMP (Arsenal) | ||
| +2 | Robbie KEANE (Coventry City) | |
| +1 | Tommy MOONEY (Watford) | |
| +1 | Gary SPEED (Newcastle United) | |
| +1 | Marians PAHARS (Southampton) | |
| Christian ZIEGE (Middlesbrough) | ||
| +2 | Roy KEANE (Manchester United) | |
| +1 | Emile HESKEY (Leicester City) | |
| Gustavo POYET (Chelsea) | ||
| Steffen IVERSEN (Tottenham Hotspur) | ||
| Julian JOACHIM (Aston Villa) | ||
| +1 | Øyvind LEONHARDSEN (Tottenham Hotspur) | |
| +1 | Les FERDINAND (Tottenham Hotspur) |
| Saturday, 21 August 1999 | |||||
| 4 | Chelsea | 1-0 | Aston Villa | ||
| 52(og) | Ehiogu | ||||
| 4 | Coventry City | 2-0 | Derby County | ||
| 43 | Keane | ||||
| 67 | Keane | ||||
| 4 | Everton | 4-1 | Southampton | ||
| 36 | Gough | 70 | Pahars | ||
| 47(og) | Lundekvam | ||||
| 48 | Jeffers | ||||
| 54 | Campbell | ||||
| 4 | Leeds United | 2-1 | Sunderland | ||
| 52 | Bowyer | 37(p) | Phillips | ||
| 71 | Mills | ||||
| 4 | Middlesbrough | 1-0 | Liverpool | ||
| 49 | Deane | ||||
| 4 | Newcastle United | 3-3 | Wimbledon | ||
| 7 | Speed | 44 | Hughes | ||
| 28 | Domi | 68 | Ainsworth | ||
| 46(p) | Solano | 90 | Ainsworth | ||
| 4 | Sheffield Wednesday | 1-2 | Tottenham Hotspur | ||
| 23(p) | Carbone | 19 | Ferdinand | ||
| 41 | Leonhardsen | ||||
| 4 | Watford | 1-0 | Bradford City | ||
| 71 | Mooney | ||||
| 4 | West Ham United | 2-1 | Leicester City | ||
| 29 | Wanchope | 2 | Heskey | ||
| 53 | Di Canio | ||||
| Sunday, 22 August 1999 | |||||
| 4 | Arsenal | 1-2 | Manchester United | ||
| 41 | Ljungberg | 58 | Keane | ||
| 88 | Keane | ||||