1. Round 15/08/1998 Middlesbrough FC - Leeds United 0:0 yellow card
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 Goal
5. Round 13/09/1998 Tottenham Hotspur - Middlesbrough FC 0:3
6. Round 19/09/1998 Middlesbrough FC - Everton FC 2:2 yellow card
7. Round 26/09/1998 Chelsea FC - Middlesbrough FC 2:0 yellow card
8. Round 03/10/1998 Middlesbrough FC - Sheffield Wednesday 4:0 Goal
11. Round 01/11/1998 Middlesbrough FC - Nottingham Forest 1:1 yellow card
12. Round 07/11/1998 Southampton FC - Middlesbrough FC 3:3 Goal yellow card
13. Round 14/11/1998 Charlton Athletic - Middlesbrough FC 1:1 yellow card
15. Round 29/11/1998 Arsenal FC - Middlesbrough FC 1:1 yellow card
16. Round 06/12/1998 Middlesbrough FC - Newcastle United 2:2
17. Round 12/12/1998 Middlesbrough FC - West Ham United 1:0
19. Round 26/12/1998 Middlesbrough FC - Liverpool FC 1:3 yellow card
20. Round 28/12/1998 Derby County - Middlesbrough FC 2:1
21. Round 09/01/1999 Middlesbrough FC - Aston Villa 0:0 yellow card
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 yellow card
27. Round 27/02/1999 Sheffield Wednesday - Middlesbrough FC 3:1 yellow card
31. Round 03/04/1999 Blackburn Rovers - Middlesbrough FC 0:0 yellow card
32. Round 05/04/1999 Middlesbrough FC - Wimbledon FC 3:1
33. Round 10/04/1999 Middlesbrough FC - Charlton Athletic 2:0