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