1. Round 03/10/1999 Sydney Olympic Lions - Newcastle Breakers 2:2
2. Round 08/10/1999 Canberra Cosmos - Sydney Olympic Lions 0:1
3. Round 16/10/1999 Wollongong City Wolves - Sydney Olympic Lions 0:4 GoalGoalGoal
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 Goal
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
11. Round 10/12/1999 Canberra Cosmos - Sydney Olympic Lions 1:3 Goal
12. Round 19/12/1999 Sydney Olympic Lions - Brisbane Strikers 2:0 Goal
13. Round 28/12/1999 Parramatta Power - Sydney Olympic Lions 1:2
14. Round 02/01/2000 Sydney Olympic Lions - Perth Glory 1:1 Goal
15. Round 07/01/2000 Newcastle Breakers - Sydney Olympic Lions 3:2
17. Round 23/01/2000 Sydney Olympic Lions - South Melbourne Lakers 6:0 GoalGoal
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 Goal
20. Round 06/02/2000 Sydney Olympic Lions - Canberra Cosmos 7:3 GoalGoalGoal
22. Round 20/02/2000 Wollongong City Wolves - Sydney Olympic Lions 1:1
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 Goal
26. Round 19/03/2000 Marconi-Fairfield Stallions - Sydney Olympic Lions 3:1 Goal
27. Round 26/03/2000 Sydney Olympic Lions - Melbourne Knights 0:1
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 Goal
30. Round 15/04/2000 Brisbane Strikers - Sydney Olympic Lions 2:2
31. Round 22/04/2000 Sydney Olympic Lions - Parramatta Power 2:1 Goal
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 Goal