1. Round 15/08/1998 Middlesbrough FC - Leeds United 0:0
2. Round 23/08/1998 Aston Villa - Middlesbrough FC 3:1
3. Round 29/08/1998 Middlesbrough FC - Derby County 1:1
4. Round 09/09/1998 Leicester City - Middlesbrough FC 0:1
5. Round 13/09/1998 Tottenham Hotspur - Middlesbrough FC 0:3
6. Round 19/09/1998 Middlesbrough FC - Everton FC 2:2
7. Round 26/09/1998 Chelsea FC - Middlesbrough FC 2:0
8. Round 03/10/1998 Middlesbrough FC - Sheffield Wednesday 4:0
13. Round 14/11/1998 Charlton Athletic - Middlesbrough FC 1:1
14. Round 21/11/1998 Middlesbrough FC - Coventry City 2:0
15. Round 29/11/1998 Arsenal FC - Middlesbrough FC 1:1
16. Round 06/12/1998 Middlesbrough FC - Newcastle United 2:2
17. Round 12/12/1998 Middlesbrough FC - West Ham United 1:0
18. Round 19/12/1998 Manchester United - Middlesbrough FC 2:3
19. Round 26/12/1998 Middlesbrough FC - Liverpool FC 1:3
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
25. Round 17/02/1999 Everton FC - Middlesbrough FC 5:0
26. Round 20/02/1999 Middlesbrough FC - Tottenham Hotspur 0:0
27. Round 27/02/1999 Sheffield Wednesday - Middlesbrough FC 3:1 yellow card
29. Round 14/03/1999 Middlesbrough FC - Southampton FC 3:0
30. Round 20/03/1999 Nottingham Forest - Middlesbrough FC 1:2
31. Round 03/04/1999 Blackburn Rovers - Middlesbrough FC 0:0
32. Round 05/04/1999 Middlesbrough FC - Wimbledon FC 3:1
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