9. Round 17/10/1998 Middlesbrough FC - Blackburn Rovers 2:1
10. Round 24/10/1998 Wimbledon FC - Middlesbrough FC 2:2
11. Round 01/11/1998 Middlesbrough FC - Nottingham Forest 1:1 Goal
12. Round 07/11/1998 Southampton FC - Middlesbrough FC 3:3
13. Round 14/11/1998 Charlton Athletic - Middlesbrough FC 1:1
14. Round 21/11/1998 Middlesbrough FC - Coventry City 2:0 yellow card
15. Round 29/11/1998 Arsenal FC - Middlesbrough FC 1:1 Goal
16. Round 06/12/1998 Middlesbrough FC - Newcastle United 2:2
17. Round 12/12/1998 Middlesbrough FC - West Ham United 1:0 Goal
18. Round 19/12/1998 Manchester United - Middlesbrough FC 2:3 Goal
19. Round 26/12/1998 Middlesbrough FC - Liverpool FC 1:3 Goal
20. Round 28/12/1998 Derby County - Middlesbrough FC 2:1
21. Round 09/01/1999 Middlesbrough FC - Aston Villa 0:0
22. Round 16/01/1999 Leeds United - Middlesbrough FC 2:0
23. Round 30/01/1999 Middlesbrough FC - Leicester City 0:0
24. Round 06/02/1999 Liverpool FC - Middlesbrough FC 3:1
29. Round 14/03/1999 Middlesbrough FC - Southampton FC 3:0
30. Round 20/03/1999 Nottingham Forest - Middlesbrough FC 1:2 Goal yellow card
31. Round 03/04/1999 Blackburn Rovers - Middlesbrough FC 0:0
33. Round 10/04/1999 Middlesbrough FC - Charlton Athletic 2:0
28. Round 14/04/1999 Middlesbrough FC - Chelsea FC 0:0
34. Round 17/04/1999 Coventry City - Middlesbrough FC 1:2
35. Round 24/04/1999 Middlesbrough FC - Arsenal FC 1:6
36. Round 01/05/1999 Newcastle United - Middlesbrough FC 1:1
37. Round 09/05/1999 Middlesbrough FC - Manchester United 0:1
38. Round 16/05/1999 West Ham United - Middlesbrough FC 4:0