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