| Australia New South Wales U20 League | 2022/06/13 03:45 | Sydney Olympic U20 v Wollongong Wolves U20 | D | 1-1 |
| 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 | 2022/07/31 02:45 | Sydney Olympic U20 v Blacktown City U20 | L | 1-3 |
| Australia New South Wales U20 League | 2022/07/27 09:00 | Sydney FC U20 v Sydney Olympic U20 | L | 5-0 |
| Australia New South Wales U20 League | 2022/07/24 05:30 | Mt Druitt Town Rangers U20 v Sydney Olympic U20 | D | 0-0 |
| Australia New South Wales U20 League | 2022/07/17 02:00 | Apia L Tigers U20 v Sydney Olympic U20 | D | 1-1 |
| Australia New South Wales U20 League | 2022/07/13 08:00 | Sydney Olympic U20 v Sydney United U20 | W | 6-0 |
| Australia New South Wales U20 League | 2022/07/09 03:45 | Sydney Olympic U20 v Sydney FC U20 | L | 0-2 |
| Australia New South Wales U20 League | 2022/06/30 09:30 | Sydney Olympic U20 v Manly United U20 | W | 3-1 |
| Australia New South Wales U20 League | 2022/06/26 03:45 | Sydney Olympic U20 v Sutherland Sharks U20 | W | 4-1 |
| Australia New South Wales U20 League | 2022/08/06 09:30 | Marconi Stallions U20 v Wollongong Wolves U20 | L | 1-0 |
| Australia New South Wales U20 League | 2022/07/31 03:00 | Wollongong Wolves U20 v Sutherland Sharks U20 | W | 5-0 |
| Australia New South Wales U20 League | 2022/07/24 03:00 | Blacktown City U20 v Wollongong Wolves U20 | L | 1-0 |
| Australia New South Wales U20 League | 2022/07/15 07:30 | Wollongong Wolves U20 v Marconi Stallions U20 | L | 1-2 |
| Australia New South Wales U20 League | 2022/07/08 08:00 | Mt Druitt Town Rangers U20 v Wollongong Wolves U20 | L | 1-0 |
| Australia New South Wales U20 League | 2022/07/01 07:30 | Wollongong Wolves U20 v Rockdale Ilinden FC U20 | W | 2-0 |
| Australia New South Wales U20 League | 2022/06/25 06:00 | Wollongong Wolves U20 v Manly United U20 | W | 4-2 |
| Australia New South Wales U20 League | 2022/06/19 02:30 | Wollongong Wolves U20 v Apia L Tigers U20 | D | 2-2 |