| Australia New South Wales U20 League | 2022/04/27 07:30 | Wollongong Wolves U20 v Sydney Olympic U20 | W | 1-2 |
| 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 | 2021/04/06 08:45 | Sydney Olympic U20 v Wollongong Wolves U20 | W | 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 | L | 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 | W | 1-0 |
| Australia New South Wales U20 League | 2018/08/05 03:00 | Wollongong Wolves U20 v Sydney Olympic U20 | L | 1-0 |
| Australia New South Wales U20 League | 2022/06/04 03:00 | Bull FC Academy U20 v Sydney Olympic U20 | L | 2-1 |
| Australia New South Wales U20 League | 2022/05/29 04:00 | Rockdale Ilinden FC U20 v Sydney Olympic U20 | D | 1-1 |
| Australia New South Wales U20 League | 2022/05/21 07:00 | Manly United U20 v Sydney Olympic U20 | L | 2-1 |
| Australia New South Wales U20 League | 2022/05/15 03:00 | Blacktown City U20 v Sydney Olympic U20 | L | 3-1 |
| Australia New South Wales U20 League | 2022/05/10 09:30 | Marconi Stallions U20 v Sydney Olympic U20 | W | 1-2 |
| Australia New South Wales U20 League | 2022/05/07 09:00 | Sydney Olympic U20 v Mt Druitt Town Rangers U20 | W | 3-1 |
| Australia New South Wales U20 League | 2022/05/01 01:00 | Sydney Olympic U20 v Apia L Tigers U20 | W | 2-0 |
| Australia New South Wales U20 League | 2022/04/27 07:30 | Wollongong Wolves U20 v Sydney Olympic U20 | W | 1-2 |
| Australia New South Wales U20 League | 2022/06/08 09:00 | Marconi Stallions U20 v Wollongong Wolves U20 | L | 3-0 |
| Australia New South Wales U20 League | 2022/06/05 06:30 | Sydney FC U20 v Wollongong Wolves U20 | D | 2-2 |
| Australia New South Wales U20 League | 2022/05/27 07:30 | Wollongong Wolves U20 v Bull FC Academy U20 | L | 1-3 |
| Australia New South Wales U20 League | 2022/05/21 08:30 | Wollongong Wolves U20 v Sydney United U20 | W | 3-1 |
| Australia New South Wales U20 League | 2022/05/14 03:30 | Sutherland Sharks U20 v Wollongong Wolves U20 | W | 0-1 |
| Australia New South Wales U20 League | 2022/05/06 07:30 | Wollongong Wolves U20 v Blacktown City U20 | L | 0-1 |
| Australia New South Wales U20 League | 2022/04/27 07:30 | Wollongong Wolves U20 v Sydney Olympic U20 | L | 1-2 |
| Australia New South Wales U20 League | 2022/04/22 07:30 | Wollongong Wolves U20 v Mt Druitt Town Rangers U20 | W | 3-2 |