1. Round 08/08/1999 Everton FC - Manchester United 1:1
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
7. Round 11/09/1999 Liverpool FC - Manchester United 2:3
9. Round 25/09/1999 Manchester United - Southampton FC 3:3
10. Round 03/10/1999 Chelsea FC - Manchester United 5:0 red card
11. Round 16/10/1999 Manchester United - Watford FC 4:1
15. Round 20/11/1999 Derby County - Manchester United 1:2 Goal yellow card
17. Round 04/12/1999 Manchester United - Everton FC 5:1 yellow card
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 Goal
23. Round 24/01/2000 Manchester United - Arsenal FC 1:1
21. Round 29/01/2000 Manchester United - Middlesbrough FC 1:0
16. Round 02/02/2000 Sheffield Wednesday - Manchester United 0:1
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
28. Round 11/03/2000 Manchester United - Derby County 3:1
29. Round 18/03/2000 Leicester City - Manchester United 0:2
31. Round 01/04/2000 Manchester United - West Ham United 7:1
32. Round 10/04/2000 Middlesbrough FC - Manchester United 3:4
33. Round 15/04/2000 Manchester United - Sunderland AFC 4:0 Goal
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 red card
37. Round 06/05/2000 Manchester United - Tottenham Hotspur 3:1