| 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 | 2023/04/22 23:00 | Apia L Tigers U20 v Sydney Olympic U20 | W | 1-2 |
| Australia New South Wales U20 League | 2023/04/06 07:45 | Mt Druitt Town Rangers U20 v Sydney Olympic U20 | L | 3-1 |
| Australia New South Wales U20 League | 2023/04/01 05:30 | Sydney Olympic U20 v Bull FC Academy U20 | L | 0-3 |
| Australia New South Wales U20 League | 2023/03/25 05:30 | Sydney Olympic U20 v NWS Spirit FC U20 | D | 1-1 |
| Australia New South Wales U20 League | 2023/03/19 06:00 | Blacktown City U20 v Sydney Olympic U20 | W | 1-3 |
| Australia New South Wales U20 League | 2023/03/11 06:00 | Western Sydney Wanderers U20 v Sydney Olympic U20 | L | 3-2 |
| Australia New South Wales U20 League | 2023/03/04 06:00 | St George City FA U20 v Sydney Olympic U20 | W | 0-1 |
| Australia New South Wales U20 League | 2023/02/26 01:45 | Sydney Olympic U20 v Rockdale Ilinden FC U20 | L | 2-5 |
| Australia New South Wales U20 League | 2023/04/25 08:59 | Wollongong Wolves U20 v Sydney United U20 | W | 2-1 |
| Australia New South Wales U20 League | 2023/04/22 07:00 | Manly United U20 v Wollongong Wolves U20 | L | 3-0 |
| Australia New South Wales U20 League | 2023/04/01 08:49 | NWS Spirit FC U20 v Wollongong Wolves U20 | D | 1-1 |
| Australia New South Wales U20 League | 2023/03/18 06:00 | St George City FA U20 v Wollongong Wolves U20 | L | 3-2 |
| Australia New South Wales U20 League | 2023/03/10 06:30 | Wollongong Wolves U20 v Rockdale Ilinden FC U20 | W | 2-1 |
| Australia New South Wales U20 League | 2023/02/25 04:00 | Bull FC Academy U20 v Wollongong Wolves U20 | W | 2-3 |
| Australia New South Wales U20 League | 2023/02/17 06:30 | Wollongong Wolves U20 v Marconi Stallions U20 | L | 1-5 |
| Australia New South Wales U20 League | 2023/02/11 05:10 | Sutherland Sharks U20 v Wollongong Wolves U20 | D | 1-1 |