2. Round 11/08/1999 Manchester United - Sheffield Wednesday 4:0
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
8. Round 18/09/1999 Manchester United - Wimbledon FC 1:1
9. Round 25/09/1999 Manchester United - Southampton FC 3:3 Goal
10. Round 03/10/1999 Chelsea FC - Manchester United 5:0
17. Round 04/12/1999 Manchester United - Everton FC 5:1
18. Round 18/12/1999 West Ham United - Manchester United 2:4
19. Round 26/12/1999 Manchester United - Bradford City 4:0
20. Round 28/12/1999 Sunderland AFC - Manchester United 2:2
23. Round 24/01/2000 Manchester United - Arsenal FC 1:1 Goal
21. Round 29/01/2000 Manchester United - Middlesbrough FC 1:0
16. Round 02/02/2000 Sheffield Wednesday - Manchester United 0:1 Goal
24. Round 05/02/2000 Manchester United - Coventry City 3:2
25. Round 12/02/2000 Newcastle United - Manchester United 3:0
22. Round 20/02/2000 Leeds United - Manchester United 0:1
26. Round 26/02/2000 Wimbledon FC - Manchester United 2:2
27. Round 04/03/2000 Manchester United - Liverpool FC 1:1
29. Round 18/03/2000 Leicester City - Manchester United 0:2
31. Round 01/04/2000 Manchester United - West Ham United 7:1
33. Round 15/04/2000 Manchester United - Sunderland AFC 4:0
34. Round 22/04/2000 Southampton FC - Manchester United 1:3
36. Round 29/04/2000 Watford FC - Manchester United 2:3
37. Round 06/05/2000 Manchester United - Tottenham Hotspur 3:1 Goal
38. Round 14/05/2000 Aston Villa - Manchester United 0:1 Goal