1. Round 15/08/1998 Wimbledon FC - Tottenham Hotspur 3:1
2. Round 22/08/1998 Tottenham Hotspur - Sheffield Wednesday 0:3
3. Round 29/08/1998 Everton FC - Tottenham Hotspur 0:1
5. Round 13/09/1998 Tottenham Hotspur - Middlesbrough FC 0:3
6. Round 19/09/1998 Southampton FC - Tottenham Hotspur 1:1
7. Round 26/09/1998 Tottenham Hotspur - Leeds United 3:3 Goal
8. Round 03/10/1998 Derby County - Tottenham Hotspur 0:1 Goal
9. Round 19/10/1998 Leicester City - Tottenham Hotspur 2:1
10. Round 24/10/1998 Tottenham Hotspur - Newcastle United 2:0
11. Round 02/11/1998 Tottenham Hotspur - Charlton Athletic 2:2
12. Round 07/11/1998 Aston Villa - Tottenham Hotspur 3:2
13. Round 14/11/1998 Arsenal FC - Tottenham Hotspur 0:0
14. Round 21/11/1998 Tottenham Hotspur - Nottingham Forest 2:0
15. Round 28/11/1998 West Ham United - Tottenham Hotspur 2:1
16. Round 05/12/1998 Tottenham Hotspur - Liverpool FC 2:1
17. Round 12/12/1998 Tottenham Hotspur - Manchester United 2:2 GoalGoal
18. Round 19/12/1998 Chelsea FC - Tottenham Hotspur 2:0
19. Round 26/12/1998 Coventry City - Tottenham Hotspur 1:1 Goal
20. Round 28/12/1998 Tottenham Hotspur - Everton FC 4:1
21. Round 09/01/1999 Sheffield Wednesday - Tottenham Hotspur 0:0
22. Round 16/01/1999 Tottenham Hotspur - Wimbledon FC 0:0
23. Round 30/01/1999 Blackburn Rovers - Tottenham Hotspur 1:1
24. Round 06/02/1999 Tottenham Hotspur - Coventry City 0:0
26. Round 20/02/1999 Middlesbrough FC - Tottenham Hotspur 0:0
27. Round 27/02/1999 Tottenham Hotspur - Derby County 1:1
25. Round 02/03/1999 Tottenham Hotspur - Southampton FC 3:0
28. Round 10/03/1999 Leeds United - Tottenham Hotspur 2:0
29. Round 13/03/1999 Tottenham Hotspur - Aston Villa 1:0
31. Round 03/04/1999 Tottenham Hotspur - Leicester City 0:2
32. Round 05/04/1999 Newcastle United - Tottenham Hotspur 1:1
34. Round 17/04/1999 Nottingham Forest - Tottenham Hotspur 0:1
30. Round 20/04/1999 Charlton Athletic - Tottenham Hotspur 1:4 Goal
35. Round 24/04/1999 Tottenham Hotspur - West Ham United 1:2
36. Round 01/05/1999 Liverpool FC - Tottenham Hotspur 3:2
33. Round 05/05/1999 Tottenham Hotspur - Arsenal FC 1:3
37. Round 10/05/1999 Tottenham Hotspur - Chelsea FC 2:2
38. Round 16/05/1999 Manchester United - Tottenham Hotspur 2:1