1. Round 07/08/1999 West Ham United - Tottenham Hotspur 1:0 yellow card
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 yellow card
6. Round 28/08/1999 Tottenham Hotspur - Leeds United 1:2 yellow card
7. Round 12/09/1999 Bradford City - Tottenham Hotspur 1:1 yellow card
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
12. Round 23/10/1999 Tottenham Hotspur - Manchester United 3:1 yellow card
13. Round 31/10/1999 Sunderland AFC - Tottenham Hotspur 2:1
15. Round 20/11/1999 Southampton FC - Tottenham Hotspur 0:1
16. Round 28/11/1999 Newcastle United - Tottenham Hotspur 2:1
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
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 yellow card
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
32. Round 09/04/2000 Liverpool FC - Tottenham Hotspur 2:0 yellow card
33. Round 15/04/2000 Tottenham Hotspur - Aston Villa 2:4
35. Round 19/04/2000 Leicester City - Tottenham Hotspur 0:1
34. Round 22/04/2000 Tottenham Hotspur - Wimbledon FC 2:0
37. Round 06/05/2000 Manchester United - Tottenham Hotspur 3:1 yellow card
38. Round 14/05/2000 Tottenham Hotspur - Sunderland AFC 3:1