1. Round 07/08/1999 Chelsea FC - Sunderland AFC 4:0
3. Round 14/08/1999 Leicester City - Chelsea FC 2:2
4. Round 21/08/1999 Chelsea FC - Aston Villa 1:0
6. Round 28/08/1999 Wimbledon FC - Chelsea FC 0:1
7. Round 11/09/1999 Chelsea FC - Newcastle United 1:0
8. Round 18/09/1999 Watford FC - Chelsea FC 1:0
9. Round 25/09/1999 Middlesbrough FC - Chelsea FC 0:1
10. Round 03/10/1999 Chelsea FC - Manchester United 5:0
11. Round 16/10/1999 Liverpool FC - Chelsea FC 1:0
12. Round 23/10/1999 Chelsea FC - Arsenal FC 2:3
13. Round 30/10/1999 Derby County - Chelsea FC 3:1
14. Round 07/11/1999 Chelsea FC - West Ham United 0:0
15. Round 20/11/1999 Everton FC - Chelsea FC 1:1
16. Round 28/11/1999 Chelsea FC - Bradford City 1:0
17. Round 04/12/1999 Sunderland AFC - Chelsea FC 4:1
18. Round 19/12/1999 Chelsea FC - Leeds United 0:2
19. Round 26/12/1999 Southampton FC - Chelsea FC 1:2
20. Round 29/12/1999 Chelsea FC - Sheffield Wednesday 3:0
21. Round 04/01/2000 Coventry City - Chelsea FC 2:2
2. Round 08/01/2000 Bradford City - Chelsea FC 1:1
5. Round 12/01/2000 Chelsea FC - Tottenham Hotspur 1:0
22. Round 15/01/2000 Chelsea FC - Leicester City 1:1
23. Round 22/01/2000 Aston Villa - Chelsea FC 0:0
24. Round 05/02/2000 Tottenham Hotspur - Chelsea FC 0:1
25. Round 12/02/2000 Chelsea FC - Wimbledon FC 3:1
26. Round 26/02/2000 Chelsea FC - Watford FC 2:1
27. Round 04/03/2000 Newcastle United - Chelsea FC 0:1
28. Round 11/03/2000 Chelsea FC - Everton FC 1:1
29. Round 18/03/2000 West Ham United - Chelsea FC 0:0
30. Round 25/03/2000 Chelsea FC - Southampton FC 1:1
31. Round 01/04/2000 Leeds United - Chelsea FC 0:1
32. Round 12/04/2000 Chelsea FC - Coventry City 2:1
33. Round 15/04/2000 Sheffield Wednesday - Chelsea FC 1:0 yellow card
34. Round 22/04/2000 Chelsea FC - Middlesbrough FC 1:1
35. Round 24/04/2000 Manchester United - Chelsea FC 3:2
36. Round 29/04/2000 Chelsea FC - Liverpool FC 2:0
37. Round 06/05/2000 Arsenal FC - Chelsea FC 2:1