1. Round 07/08/1999 Sheffield Wednesday - Liverpool FC 1:2
2. Round 11/08/1999 Manchester United - Sheffield Wednesday 4:0
3. Round 14/08/1999 Bradford City - Sheffield Wednesday 1:1
4. Round 21/08/1999 Sheffield Wednesday - Tottenham Hotspur 1:2
5. Round 25/08/1999 Sheffield Wednesday - Derby County 0:2
7. Round 11/09/1999 Sheffield Wednesday - Everton FC 0:2
8. Round 19/09/1999 Newcastle United - Sheffield Wednesday 8:0
9. Round 25/09/1999 Sunderland AFC - Sheffield Wednesday 1:0
10. Round 02/10/1999 Sheffield Wednesday - Wimbledon FC 5:1
11. Round 16/10/1999 Leeds United - Sheffield Wednesday 2:0
12. Round 23/10/1999 Sheffield Wednesday - Coventry City 0:0
13. Round 30/10/1999 Leicester City - Sheffield Wednesday 3:0
14. Round 06/11/1999 Sheffield Wednesday - Watford FC 2:2
15. Round 21/11/1999 West Ham United - Sheffield Wednesday 4:3
17. Round 05/12/1999 Liverpool FC - Sheffield Wednesday 4:1
18. Round 18/12/1999 Aston Villa - Sheffield Wednesday 2:1
19. Round 26/12/1999 Sheffield Wednesday - Middlesbrough FC 1:0
20. Round 29/12/1999 Chelsea FC - Sheffield Wednesday 3:0
21. Round 03/01/2000 Sheffield Wednesday - Arsenal FC 1:1
22. Round 15/01/2000 Sheffield Wednesday - Bradford City 2:0
23. Round 22/01/2000 Tottenham Hotspur - Sheffield Wednesday 0:1
16. Round 02/02/2000 Sheffield Wednesday - Manchester United 0:1
24. Round 05/02/2000 Derby County - Sheffield Wednesday 3:3
25. Round 12/02/2000 Sheffield Wednesday - Southampton FC 0:1
26. Round 26/02/2000 Sheffield Wednesday - Newcastle United 0:2
27. Round 04/03/2000 Everton FC - Sheffield Wednesday 1:1
28. Round 11/03/2000 Sheffield Wednesday - West Ham United 3:1
29. Round 18/03/2000 Watford FC - Sheffield Wednesday 1:0
30. Round 25/03/2000 Middlesbrough FC - Sheffield Wednesday 1:0
31. Round 05/04/2000 Sheffield Wednesday - Aston Villa 0:1
35. Round 12/04/2000 Wimbledon FC - Sheffield Wednesday 0:2
33. Round 15/04/2000 Sheffield Wednesday - Chelsea FC 1:0
34. Round 22/04/2000 Sheffield Wednesday - Sunderland AFC 0:2
36. Round 30/04/2000 Sheffield Wednesday - Leeds United 0:3
37. Round 06/05/2000 Coventry City - Sheffield Wednesday 4:1
32. Round 09/05/2000 Arsenal FC - Sheffield Wednesday 3:3
38. Round 14/05/2000 Sheffield Wednesday - Leicester City 4:0