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