| Australia New South Wales U20 League | 2021/06/06 02:30 | Wollongong Wolves U20 v Sydney Olympic U20 | W | 3-0 |
| Australia New South Wales U20 League | 2021/04/06 08:45 | Sydney Olympic U20 v Wollongong Wolves U20 | L | 4-1 |
| Australia New South Wales U20 League | 2020/09/20 02:30 | Wollongong Wolves U20 v Sydney Olympic U20 | D | 1-1 |
| 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 | 2022/04/22 07:30 | Wollongong Wolves U20 v Mt Druitt Town Rangers U20 | W | 3-2 |
| Australia New South Wales U20 League | 2022/04/17 04:00 | Rockdale Ilinden FC U20 v Wollongong Wolves U20 | W | 0-3 |
| Australia New South Wales U20 League | 2022/04/09 07:00 | Manly United U20 v Wollongong Wolves U20 | L | 2-1 |
| Australia New South Wales U20 League | 2022/03/18 06:30 | Wollongong Wolves U20 v Sydney FC U20 | W | 2-0 |
| Australia New South Wales U20 League | 2022/03/11 23:00 | Bull FC Academy U20 v Wollongong Wolves U20 | W | 1-2 |
| Australia New South Wales U20 League | 2022/03/06 02:00 | Sydney United U20 v Wollongong Wolves U20 | W | 0-3 |
| Australia New South Wales U20 League | 2021/06/20 02:30 | Wollongong Wolves U20 v Marconi Stallions U20 | W | 2-1 |
| Australia New South Wales U20 League | 2021/06/14 03:00 | Bull FC Academy U20 v Wollongong Wolves U20 | W | 1-4 |
| Australia New South Wales U20 League | 2022/04/18 03:00 | Sydney United U20 v Sydney Olympic U20 | W | 0-2 |
| Australia New South Wales U20 League | 2022/04/09 03:30 | Sutherland Sharks U20 v Sydney Olympic U20 | L | 2-0 |
| Australia New South Wales U20 League | 2022/03/20 02:45 | Sydney Olympic U20 v Bull FC Academy U20 | L | 0-2 |
| Australia New South Wales U20 League | 2022/03/13 02:45 | Sydney Olympic U20 v Rockdale Ilinden FC U20 | W | 2-1 |
| Australia New South Wales U20 League | 2021/06/20 03:45 | Sydney Olympic U20 v Mt Druitt Town Rangers U20 | W | 1-0 |
| Australia New South Wales U20 League | 2021/06/12 05:15 | Sydney Olympic U20 v Sydney FC U20 | D | 0-0 |
| Australia New South Wales U20 League | 2021/06/06 02:30 | Wollongong Wolves U20 v Sydney Olympic U20 | L | 3-0 |
| Australia New South Wales U20 League | 2021/05/30 01:00 | Apia L Tigers U20 v Sydney Olympic U20 | L | 2-0 |