1. Round 03/10/1999 Sydney Olympic Lions - Newcastle Breakers 2:2
3. Round 16/10/1999 Wollongong City Wolves - Sydney Olympic Lions 0:4 Goal
4. Round 24/10/1999 Sydney Olympic Lions - Wollongong City Wolves 1:1
5. Round 29/10/1999 Northern Spirit - Sydney Olympic Lions 0:1
6. Round 07/11/1999 Sydney Olympic Lions - Auckland Football Kingz 1:2
7. Round 12/11/1999 Gippsland Falcons - Sydney Olympic Lions 0:1
8. Round 21/11/1999 Sydney Olympic Lions - Marconi-Fairfield Stallions 2:1
9. Round 28/11/1999 Melbourne Knights - Sydney Olympic Lions 2:1
10. Round 05/12/1999 Sydney Olympic Lions - Adelaide City Force 2:0 Goal
11. Round 10/12/1999 Canberra Cosmos - Sydney Olympic Lions 1:3
12. Round 19/12/1999 Sydney Olympic Lions - Brisbane Strikers 2:0
17. Round 23/01/2000 Sydney Olympic Lions - South Melbourne Lakers 6:0 Goal
18. Round 26/01/2000 South Melbourne Lakers - Sydney Olympic Lions 2:0
19. Round 28/01/2000 Carlton Blues - Sydney Olympic Lions 0:1
20. Round 06/02/2000 Sydney Olympic Lions - Canberra Cosmos 7:3 GoalGoal
21. Round 13/02/2000 Sydney Olympic Lions - Wollongong City Wolves 2:2
22. Round 20/02/2000 Wollongong City Wolves - Sydney Olympic Lions 1:1 Goal
23. Round 27/02/2000 Sydney Olympic Lions - Northern Spirit 3:1 Goal
24. Round 03/03/2000 Auckland Football Kingz - Sydney Olympic Lions 2:0
25. Round 12/03/2000 Sydney Olympic Lions - Gippsland Falcons 1:0
26. Round 19/03/2000 Marconi-Fairfield Stallions - Sydney Olympic Lions 3:1
28. Round 31/03/2000 Adelaide City Force - Sydney Olympic Lions 2:0
29. Round 09/04/2000 Sydney Olympic Lions - Canberra Cosmos 1:1
30. Round 15/04/2000 Brisbane Strikers - Sydney Olympic Lions 2:2 GoalGoal
31. Round 22/04/2000 Sydney Olympic Lions - Parramatta Power 2:1
32. Round 25/04/2000 Perth Glory - Sydney Olympic Lions 1:0
33. Round 30/04/2000 Sydney Olympic Lions - Carlton Blues 0:2
34. Round 07/05/2000 Sydney Olympic Lions - Sydney United Pumas 3:0