| Australia New South Wales U20 League | 2025/06/04 10:00 | Manly United U20 v Sydney Olympic U20 | W | 3-0 |
| Australia New South Wales U20 League | 2024/07/22 09:30 | Sydney Olympic U20 v Manly United U20 | W | 1-4 |
| Australia New South Wales U20 League | 2024/03/22 06:30 | Manly United U20 v Sydney Olympic U20 | W | 2-0 |
| Australia New South Wales U20 League | 2023/05/27 06:30 | Sydney Olympic U20 v Manly United U20 | W | 0-3 |
| Australia New South Wales U20 League | 2023/02/11 06:00 | Manly United U20 v Sydney Olympic U20 | D | 1-1 |
| Australia New South Wales U20 League | 2022/06/30 09:30 | Sydney Olympic U20 v Manly United U20 | L | 3-1 |
| Australia New South Wales U20 League | 2022/05/21 07:00 | Manly United U20 v Sydney Olympic U20 | W | 2-1 |
| Australia New South Wales U20 League | 2021/04/10 07:00 | Manly United U20 v Sydney Olympic U20 | W | 1-0 |
| Australia New South Wales U20 League | 2025/08/02 10:00 | Apia L Tigers U20 v Manly United U20 | W | 1-2 |
| Australia New South Wales U20 League | 2025/07/25 07:30 | Manly United U20 v Western Sydney Wanderers U20 | W | 1-0 |
| Australia New South Wales U20 League | 2025/07/11 07:30 | Manly United U20 v Blacktown City U20 | W | 2-0 |
| Australia New South Wales U20 League | 2025/07/05 09:45 | NWS Spirit FC U20 v Manly United U20 | D | 3-3 |
| Australia New South Wales U20 League | 2025/06/27 07:30 | Manly United U20 v St George City FA U20 | W | 3-1 |
| Australia New South Wales U20 League | 2025/06/21 09:00 | Mt Druitt Town Rangers U20 v Manly United U20 | W | 1-2 |
| Australia New South Wales U20 League | 2025/06/08 03:00 | Sydney United U20 v Manly United U20 | W | 1-2 |
| Australia New South Wales U20 League | 2025/06/04 10:00 | Manly United U20 v Sydney Olympic U20 | W | 3-0 |
| Australia New South Wales U20 League | 2025/08/02 09:45 | NWS Spirit FC U20 v Sydney Olympic U20 | L | 2-1 |
| Australia New South Wales U20 League | 2025/07/28 08:00 | Sydney Olympic U20 v St George City FA U20 | L | 2-5 |
| Australia New South Wales U20 League | 2025/07/20 09:17 | Sydney Olympic U20 v Mt Druitt Town Rangers U20 | W | 3-1 |
| Australia New South Wales U20 League | 2025/07/04 07:30 | Sydney FC U20 v Sydney Olympic U20 | L | 3-1 |
| Australia New South Wales U20 League | 2025/06/27 09:30 | Sydney Olympic U20 v Blacktown City U20 | W | 2-0 |
| Australia New South Wales U20 League | 2025/06/20 09:30 | Sydney Olympic U20 v Marconi Stallions U20 | D | 2-2 |
| Australia New South Wales U20 League | 2025/06/16 09:30 | Sydney Olympic U20 v Sutherland Sharks U20 | L | 1-3 |
| Australia New South Wales U20 League | 2025/06/07 07:00 | Wollongong Wolves U20 v Sydney Olympic U20 | W | 0-2 |