| 2. Round | 08/10/1999 | Canberra Cosmos | - | Sydney Olympic Lions | 0:1 | ||||
| 16. Round | 16/01/2000 | Sydney United Pumas | - | Sydney Olympic Lions | 2:0 | ||||
| 23. Round | 27/02/2000 | Sydney Olympic Lions | - | Northern Spirit | 3:1 | ||||
| 24. Round | 03/03/2000 | Auckland Football Kingz | - | Sydney Olympic Lions | 2:0 |
Australia