| Australia New South Wales U20 League | 2020/03/01 02:51 | Sydney Olympic U20 v Wollongong Wolves U20 | W | 0-3 |
| Australia New South Wales U20 League | 2019/06/23 03:03 | Wollongong Wolves U20 v Sydney Olympic U20 | D | 1-1 |
| Australia New South Wales U20 League | 2019/04/07 03:56 | Sydney Olympic U20 v Wollongong Wolves U20 | L | 1-0 |
| Australia New South Wales U20 League | 2018/08/05 03:00 | Wollongong Wolves U20 v Sydney Olympic U20 | W | 1-0 |
| Australia New South Wales U20 League | 2018/05/13 02:45 | Sydney Olympic U20 v Wollongong Wolves U20 | D | 1-1 |
| Australia New South Wales U20 League | 2017/06/04 03:03 | Wollongong Wolves U20 v Sydney Olympic U20 | D | 2-2 |
| Australia New South Wales U20 League | 2017/03/19 01:45 | Sydney Olympic U20 v Wollongong Wolves U20 | L | 4-0 |
| Australia New South Wales U20 League | 2020/09/13 04:00 | Rockdale City Suns U20 v Wollongong Wolves U20 | L | 3-2 |
| Australia New South Wales U20 League | 2020/09/06 02:30 | Wollongong Wolves U20 v Blacktown City U20 | D | 0-0 |
| Australia New South Wales U20 League | 2020/08/30 03:00 | Sydney United U20 v Wollongong Wolves U20 | L | 2-1 |
| Australia New South Wales U20 League | 2020/08/23 02:30 | Wollongong Wolves U20 v North Shore Mariners U20 | W | 5-0 |
| Australia New South Wales U20 League | 2020/08/16 06:30 | Wollongong Wolves U20 v Marconi Stallions U20 | W | 3-0 |
| Australia New South Wales U20 League | 2020/08/09 05:00 | Apia L Tigers U20 v Wollongong Wolves U20 | L | 1-0 |
| Australia New South Wales U20 League | 2020/08/02 02:30 | Wollongong Wolves U20 v Mt Druitt Town Rangers U20 | D | 0-0 |
| Australia New South Wales U20 League | 2020/03/08 05:39 | Wollongong Wolves U20 v North Shore Mariners U20 | W | 3-2 |
| Australia New South Wales U20 League | 2020/09/13 03:00 | Sydney Olympic U20 v Apia L Tigers U20 | W | 4-0 |
| Australia New South Wales U20 League | 2020/09/05 04:00 | Marconi Stallions U20 v Sydney Olympic U20 | D | 1-1 |
| Australia New South Wales U20 League | 2020/08/30 06:55 | Sydney Olympic U20 v Rockdale City Suns U20 | L | 0-2 |
| Australia New South Wales U20 League | 2020/08/21 07:45 | Manly United U20 v Sydney Olympic U20 | D | 1-1 |
| Australia New South Wales U20 League | 2020/08/14 07:30 | Blacktown City U20 v Sydney Olympic U20 | D | 3-3 |
| Australia New South Wales U20 League | 2020/08/02 03:00 | Sydney United U20 v Sydney Olympic U20 | W | 2-3 |
| Australia New South Wales U20 League | 2020/03/14 04:01 | Marconi Stallions U20 v Sydney Olympic U20 | L | 2-1 |
| Australia New South Wales U20 League | 2020/03/08 04:33 | Apia L Tigers U20 v Sydney Olympic U20 | W | 1-2 |