| Australia New South Wales U20 League | 2023/08/13 10:03 | Wollongong Wolves U20 v Sydney Olympic U20 | W | 0-1 |
| Australia New South Wales U20 League | 2023/04/29 06:30 | Sydney Olympic U20 v Wollongong Wolves U20 | L | 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 | 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 | 2024/03/22 06:30 | Manly United U20 v Sydney Olympic U20 | L | 2-0 |
| Australia New South Wales U20 League | 2024/03/16 09:00 | Apia L Tigers U20 v Sydney Olympic U20 | L | 1-0 |
| Australia New South Wales U20 League | 2024/03/09 07:40 | Sutherland Sharks U20 v Sydney Olympic U20 | L | 3-0 |
| Australia New South Wales U20 League | 2024/03/05 08:00 | Sydney Olympic U20 v Marconi Stallions U20 | W | 1-0 |
| Australia New South Wales U20 League | 2024/03/02 08:00 | Sydney Olympic U20 v Sydney United U20 | W | 3-0 |
| Australia New South Wales U20 League | 2024/02/27 08:00 | Sydney Olympic U20 v St George City FA U20 | L | 2-5 |
| Australia New South Wales U20 League | 2024/02/17 03:45 | Sydney Olympic U20 v Hills United FC U20 | L | 2-4 |
| Australia New South Wales U20 League | 2023/08/25 09:00 | Sydney Olympic U20 v Sydney United U20 | L | 0-4 |
| Australia New South Wales U20 League | 2024/03/10 02:00 | Blacktown City U20 v Wollongong Wolves U20 | L | 5-2 |
| Australia New South Wales U20 League | 2024/03/05 08:30 | Sutherland Sharks U20 v Wollongong Wolves U20 | L | 6-1 |
| Australia New South Wales U20 League | 2024/03/03 02:00 | Wollongong Wolves U20 v St George City FA U20 | D | 2-2 |
| Australia New South Wales U20 League | 2023/08/27 03:00 | Wollongong Wolves U20 v Mt Druitt Town Rangers U20 | D | 0-0 |
| Australia New South Wales U20 League | 2023/08/20 03:00 | Blacktown City U20 v Wollongong Wolves U20 | W | 0-2 |
| 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 | 2023/08/06 03:00 | Wollongong Wolves U20 v Manly United U20 | D | 0-0 |
| Australia New South Wales U20 League | 2023/08/02 09:30 | Wollongong Wolves U20 v NWS Spirit FC U20 | W | 3-2 |