| Australia New South Wales U20 League | 2025/02/22 08:00 | Sydney Olympic U20 v Wollongong Wolves U20 | D | 2-2 |
| Australia New South Wales U20 League | 2024/07/07 03:00 | Wollongong Wolves U20 v Sydney Olympic U20 | L | 0-3 |
| Australia New South Wales U20 League | 2024/03/30 08:00 | Sydney Olympic U20 v Wollongong Wolves U20 | L | 5-2 |
| Australia New South Wales U20 League | 2023/08/13 10:03 | Wollongong Wolves U20 v Sydney Olympic U20 | L | 0-1 |
| Australia New South Wales U20 League | 2023/04/29 06:30 | Sydney Olympic U20 v Wollongong Wolves U20 | W | 1-4 |
| 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 | L | 1-2 |
| 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 | 2025/02/22 08:00 | Sydney Olympic U20 v Wollongong Wolves U20 | D | 2-2 |
| Australia New South Wales U20 League | 2025/02/14 06:30 | Wollongong Wolves U20 v St George City FA U20 | D | 1-1 |
| Australia New South Wales U20 League | 2025/02/08 09:00 | Apia L Tigers U20 v Wollongong Wolves U20 | L | 4-0 |
| Australia New South Wales U20 League | 2024/08/25 03:00 | Wollongong Wolves U20 v Manly United U20 | D | 4-4 |
| Australia New South Wales U20 League | 2024/08/18 03:00 | Wollongong Wolves U20 v NWS Spirit FC U20 | L | 2-3 |
| Australia New South Wales U20 League | 2024/08/04 03:00 | Wollongong Wolves U20 v Rockdale Ilinden FC U20 | L | 1-2 |
| Australia New South Wales U20 League | 2024/07/26 07:30 | Sydney FC U20 v Wollongong Wolves U20 | L | 3-1 |
| Australia New South Wales U20 League | 2024/07/24 09:30 | Wollongong Wolves U20 v Sydney United U20 | L | 1-3 |
| Australia New South Wales U20 League | 2025/03/01 06:30 | Sutherland Sharks U20 v Sydney Olympic U20 | W | 1-3 |
| Australia New South Wales U20 League | 2025/02/22 08:00 | Sydney Olympic U20 v Wollongong Wolves U20 | D | 2-2 |
| Australia New South Wales U20 League | 2025/02/15 08:00 | Sydney Olympic U20 v Western Sydney Wanderers U20 | L | 0-1 |
| Australia New South Wales U20 League | 2025/02/08 08:12 | Sydney Olympic U20 v St George Saints U20 | W | 3-1 |
| Australia New South Wales U20 League | 2024/08/23 09:00 | Sydney Olympic U20 v Sydney FC U20 | L | 2-3 |
| Australia New South Wales U20 League | 2024/08/16 09:00 | Sydney Olympic U20 v Western Sydney Wanderers U20 | L | 0-3 |
| Australia New South Wales U20 League | 2024/08/10 04:00 | Sydney Olympic U20 v St George Saints U20 | L | 0-1 |
| Australia New South Wales U20 League | 2024/08/07 09:30 | Sydney Olympic U20 v Sutherland Sharks U20 | L | 2-4 |