| 3. Round | 14/08/1999 | Manchester United | - | Leeds United | 2:0 | ||||
| 4. Round | 22/08/1999 | Arsenal FC | - | Manchester United | 1:2 | ||||
| 5. Round | 25/08/1999 | Coventry City | - | Manchester United | 1:2 | ||||
| 6. Round | 30/08/1999 | Manchester United | - | Newcastle United | 5:1 | ||||
| 15. Round | 20/11/1999 | Derby County | - | Manchester United | 1:2 | ||||
| 17. Round | 04/12/1999 | Manchester United | - | Everton FC | 5:1 | ||||
| 18. Round | 18/12/1999 | West Ham United | - | Manchester United | 2:4 | ||||
| 27. Round | 04/03/2000 | Manchester United | - | Liverpool FC | 1:1 | ||||
| 33. Round | 15/04/2000 | Manchester United | - | Sunderland AFC | 4:0 | ||||
| 34. Round | 22/04/2000 | Southampton FC | - | Manchester United | 1:3 | ||||
| 35. Round | 24/04/2000 | Manchester United | - | Chelsea FC | 3:2 | ||||
| 36. Round | 29/04/2000 | Watford FC | - | Manchester United | 2:3 | ||||
| 37. Round | 06/05/2000 | Manchester United | - | Tottenham Hotspur | 3:1 | ||||
| 38. Round | 14/05/2000 | Aston Villa | - | Manchester United | 0:1 |
Netherlands