1. Round 08/08/1999 Antalyaspor - İstanbulspor AŞ 0:3 dec.
2. Round 14/08/1999 İstanbulspor AŞ - Bursaspor 1:0
3. Round 12/09/1999 Göztepe - İstanbulspor AŞ 2:0
4. Round 19/09/1999 İstanbulspor AŞ - Fenerbahçe 1:4
5. Round 26/09/1999 Erzurumspor (1968-2015) - İstanbulspor AŞ 0:0
6. Round 17/10/1999 İstanbulspor AŞ - Gençlerbirliği 3:1
7. Round 23/10/1999 Beşiktaş - İstanbulspor AŞ 3:0 yellow card
8. Round 31/10/1999 İstanbulspor AŞ - Denizlispor 1:1
9. Round 21/11/1999 Vanspor AS - İstanbulspor AŞ 1:1 yellow card
10. Round 28/11/1999 İstanbulspor AŞ - Kocaelispor 4:1 red card
12. Round 11/12/1999 İstanbulspor AŞ - Samsunspor 0:1
13. Round 19/12/1999 İstanbulspor AŞ - Gaziantepspor 1:1
14. Round 26/12/1999 Trabzonspor - İstanbulspor AŞ 1:1
15. Round 09/01/2000 İstanbulspor AŞ - MKE Ankaragücü 2:6
16. Round 16/01/2000 Adanaspor - İstanbulspor AŞ 2:1
17. Round 23/01/2000 İstanbulspor AŞ - Galatasaray 0:0
18. Round 29/01/2000 İstanbulspor AŞ - Antalyaspor 0:0 yellow card
19. Round 05/02/2000 Bursaspor - İstanbulspor AŞ 1:0 yellow card
21. Round 19/02/2000 Fenerbahçe - İstanbulspor AŞ 1:0
22. Round 27/02/2000 İstanbulspor AŞ - Erzurumspor (1968-2015) 1:1
23. Round 04/03/2000 Gençlerbirliği - İstanbulspor AŞ 1:1
24. Round 12/03/2000 İstanbulspor AŞ - Beşiktaş 0:2
25. Round 19/03/2000 Denizlispor - İstanbulspor AŞ 3:1
26. Round 25/03/2000 İstanbulspor AŞ - Vanspor AS 0:0 yellow card
27. Round 02/04/2000 Kocaelispor - İstanbulspor AŞ 2:1
28. Round 08/04/2000 İstanbulspor AŞ - Altay Izmir 1:0 yellow card
30. Round 23/04/2000 Gaziantepspor - İstanbulspor AŞ 1:0
31. Round 29/04/2000 İstanbulspor AŞ - Trabzonspor 5:1
32. Round 07/05/2000 MKE Ankaragücü - İstanbulspor AŞ 2:2
33. Round 12/05/2000 İstanbulspor AŞ - Adanaspor 3:2
34. Round 21/05/2000 Galatasaray - İstanbulspor AŞ 1:1 yellow card