| 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 | W | 3-1 |
| Australia - New South Wales - U20 League | 2022/05/21 07:00 | Manly United U20 v Sydney Olympic U20 | L | 2-1 |
| Australia - New South Wales - U20 League | 2021/04/10 07:00 | Manly United U20 v Sydney Olympic U20 | L | 1-0 |
| Australia - New South Wales - U20 League | 2020/08/21 07:45 | Manly United U20 v Sydney Olympic U20 | D | 1-1 |
| Australia - Amicale | 2020/02/01 06:03 | Manly United U20 v Sydney Olympic U20 | D | 0-0 |
| Australia - New South Wales - U20 League | 2019/07/07 03:02 | Manly United U20 v Sydney Olympic U20 | W | 0-1 |
| Australia - New South Wales - U20 League | 2019/04/19 04:35 | Sydney Olympic U20 v Manly United U20 | W | 3-1 |
| 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 | 2023/05/14 03:00 | Sydney United U20 v Sydney Olympic U20 | L | 4-1 |
| Australia - New South Wales - U20 League | 2023/05/06 06:30 | Sydney Olympic U20 v Marconi Stallions U20 | W | 3-2 |
| 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 | 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 | 2023/05/20 09:15 | Manly United U20 v Blacktown City U20 | W | 3-1 |
| Australia - New South Wales - U20 League | 2023/04/22 07:00 | Manly United U20 v Wollongong Wolves U20 | W | 3-0 |
| Australia - New South Wales - U20 League | 2023/04/15 06:10 | Sutherland Sharks U20 v Manly United U20 | L | 3-1 |
| Australia - New South Wales - U20 League | 2023/04/07 07:15 | Apia L Tigers U20 v Manly United U20 | W | 0-3 |
| Australia - New South Wales - U20 League | 2023/04/02 07:00 | Manly United U20 v Mt Druitt Town Rangers U20 | W | 3-1 |
| Australia - New South Wales - U20 League | 2023/03/25 05:45 | Marconi Stallions U20 v Manly United U20 | D | 2-2 |
| Australia - New South Wales - U20 League | 2023/03/18 08:30 | NWS Spirit FC U20 v Manly United U20 | W | 0-1 |
| Australia - New South Wales - U20 League | 2023/03/11 06:00 | Manly United U20 v St George City FA U20 | W | 2-1 |