| 3. Jornada | 14.08.1999 | Manchester United | - | Leeds United | 2:0 | ||||
| 4. Jornada | 22.08.1999 | Arsenal | - | Manchester United | 1:2 | ||||
| 5. Jornada | 25.08.1999 | Coventry City | - | Manchester United | 1:2 | ||||
| 6. Jornada | 30.08.1999 | Manchester United | - | Newcastle United | 5:1 | ||||
| 15. Jornada | 20.11.1999 | Derby County | - | Manchester United | 1:2 | ||||
| 17. Jornada | 04.12.1999 | Manchester United | - | Everton | 5:1 | ||||
| 18. Jornada | 18.12.1999 | West Ham United | - | Manchester United | 2:4 | ||||
| 27. Jornada | 04.03.2000 | Manchester United | - | Liverpool | 1:1 | ||||
| 33. Jornada | 15.04.2000 | Manchester United | - | Sunderland | 4:0 | ||||
| 34. Jornada | 22.04.2000 | Southampton | - | Manchester United | 1:3 | ||||
| 35. Jornada | 24.04.2000 | Manchester United | - | Chelsea | 3:2 | ||||
| 36. Jornada | 29.04.2000 | Watford FC | - | Manchester United | 2:3 | ||||
| 37. Jornada | 06.05.2000 | Manchester United | - | Tottenham Hotspur | 3:1 | ||||
| 38. Jornada | 14.05.2000 | Aston Villa | - | Manchester United | 0:1 |
Países Bajos