1. Round 15/08/1998 Coventry City - Chelsea FC 2:1
2. Round 22/08/1998 Chelsea FC - Newcastle United 1:1
4. Round 09/09/1998 Chelsea FC - Arsenal FC 0:0
5. Round 12/09/1998 Chelsea FC - Nottingham Forest 2:1
6. Round 21/09/1998 Blackburn Rovers - Chelsea FC 3:4
7. Round 26/09/1998 Chelsea FC - Middlesbrough FC 2:0
8. Round 04/10/1998 Liverpool FC - Chelsea FC 1:1
9. Round 17/10/1998 Chelsea FC - Charlton Athletic 2:1
10. Round 25/10/1998 Leeds United - Chelsea FC 0:0
12. Round 08/11/1998 West Ham United - Chelsea FC 1:1
13. Round 14/11/1998 Chelsea FC - Wimbledon FC 3:0
14. Round 21/11/1998 Leicester City - Chelsea FC 2:4
15. Round 28/11/1998 Chelsea FC - Sheffield Wednesday 1:1 yellow card
16. Round 05/12/1998 Everton FC - Chelsea FC 0:0
11. Round 09/12/1998 Chelsea FC - Aston Villa 2:1
20. Round 29/12/1998 Chelsea FC - Manchester United 0:0
21. Round 09/01/1999 Newcastle United - Chelsea FC 0:1 yellow card
23. Round 31/01/1999 Arsenal FC - Chelsea FC 1:0
24. Round 06/02/1999 Chelsea FC - Southampton FC 1:0
25. Round 17/02/1999 Chelsea FC - Blackburn Rovers 1:1
26. Round 20/02/1999 Nottingham Forest - Chelsea FC 1:3
27. Round 27/02/1999 Chelsea FC - Liverpool FC 2:1
29. Round 13/03/1999 Chelsea FC - West Ham United 0:1
30. Round 21/03/1999 Aston Villa - Chelsea FC 0:3 yellow card
31. Round 03/04/1999 Charlton Athletic - Chelsea FC 0:1
28. Round 14/04/1999 Middlesbrough FC - Chelsea FC 0:0 yellow card
34. Round 18/04/1999 Chelsea FC - Leicester City 2:2
35. Round 25/04/1999 Sheffield Wednesday - Chelsea FC 0:0
36. Round 01/05/1999 Chelsea FC - Everton FC 3:1
32. Round 05/05/1999 Chelsea FC - Leeds United 1:0
37. Round 10/05/1999 Tottenham Hotspur - Chelsea FC 2:2 yellow card