| 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 | 2024/08/07 09:30 | Sydney Olympic U20 v Sutherland Sharks U20 | L | 2-4 |
| 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 | 2023/05/20 06:10 | Sutherland Sharks U20 v Sydney Olympic U20 | L | 2-0 |
| Australia New South Wales U20 League | 2023/02/05 01:45 | Sydney Olympic U20 v Sutherland Sharks U20 | D | 1-1 |
| 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 | 2022/04/09 03:30 | Sutherland Sharks U20 v Sydney Olympic U20 | L | 2-0 |
| Australia New South Wales U20 League | 2021/05/01 03:30 | Sutherland Sharks U20 v Sydney Olympic U20 | W | 0-4 |
| Australia New South Wales U20 League | 2025/04/19 09:18 | Sydney Olympic U20 v NWS Spirit FC U20 | L | 0-3 |
| Australia New South Wales U20 League | 2025/04/12 07:00 | St George City FA U20 v Sydney Olympic U20 | D | 2-2 |
| Australia New South Wales U20 League | 2025/04/05 08:14 | Mt Druitt Town Rangers U20 v Sydney Olympic U20 | W | 0-2 |
| Australia New South Wales U20 League | 2025/03/22 09:30 | Sydney Olympic U20 v Sydney FC U20 | D | 1-1 |
| Australia New South Wales U20 League | 2025/03/15 06:00 | Blacktown City U20 v Sydney Olympic U20 | W | 0-3 |
| Australia New South Wales U20 League | 2025/03/08 06:00 | Marconi Stallions U20 v Sydney Olympic U20 | D | 0-0 |
| 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 | 2025/04/25 01:30 | Sydney FC U20 v Sutherland Sharks U20 | W | 2-3 |
| Australia New South Wales U20 League | 2025/04/19 04:00 | Sutherland Sharks U20 v St George City FA U20 | L | 1-4 |
| Australia New South Wales U20 League | 2025/04/13 03:00 | Wollongong Wolves U20 v Sutherland Sharks U20 | W | 1-2 |
| Australia New South Wales U20 League | 2025/04/05 06:00 | Blacktown City U20 v Sutherland Sharks U20 | L | 3-2 |
| Australia New South Wales U20 League | 2025/03/29 08:45 | NWS Spirit FC U20 v Sutherland Sharks U20 | L | 3-0 |
| Australia New South Wales U20 League | 2025/03/23 03:00 | Sutherland Sharks U20 v Central Coast Mariners U20 | L | 0-5 |
| Australia New South Wales U20 League | 2025/03/16 05:00 | Sutherland Sharks U20 v Rockdale Ilinden FC U20 | L | 2-3 |
| Australia New South Wales U20 League | 2025/03/07 07:00 | St George Saints U20 v Sutherland Sharks U20 | L | 2-0 |