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