| Australia New South Wales U20 League | 2022/07/27 09:00 | Sydney FC U20 v Sydney Olympic U20 | W | 5-0 |
| Australia New South Wales U20 League | 2022/07/09 03:45 | Sydney Olympic U20 v Sydney FC U20 | W | 0-2 |
| Australia New South Wales U20 League | 2021/06/12 05:15 | Sydney Olympic U20 v Sydney FC U20 | D | 0-0 |
| Australia New South Wales U20 League | 2021/03/28 05:30 | Sydney FC U20 v Sydney Olympic U20 | W | 1-0 |
| Australia New South Wales U20 League | 2019/05/17 08:00 | Sydney Olympic U20 v Sydney FC U20 | W | 1-2 |
| Australia New South Wales U20 League | 2017/03/25 06:45 | Sydney FC U20 v Sydney Olympic U20 | L | 1-2 |
| Australia New South Wales U20 League | 2022/08/14 03:15 | Blacktown City U20 v Sydney FC U20 | W | 0-2 |
| Australia New South Wales U20 League | 2022/08/07 07:30 | Sydney FC U20 v Mt Druitt Town Rangers U20 | W | 4-1 |
| Australia New South Wales U20 League | 2022/07/31 06:30 | Sydney FC U20 v Mt Druitt Town Rangers U20 | W | 5-1 |
| Australia New South Wales U20 League | 2022/07/27 09:00 | Sydney FC U20 v Sydney Olympic U20 | W | 5-0 |
| Australia New South Wales U20 League | 2022/07/24 04:00 | Rockdale Ilinden FC U20 v Sydney FC U20 | W | 0-4 |
| Australia New South Wales U20 League | 2022/07/17 03:25 | Sydney FC U20 v Sydney United U20 | W | 5-0 |
| Australia New South Wales U20 League | 2022/07/09 03:45 | Sydney Olympic U20 v Sydney FC U20 | W | 0-2 |
| Australia New South Wales U20 League | 2022/07/03 06:30 | Sydney FC U20 v Blacktown City U20 | D | 1-1 |
| 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 | 2023/02/05 01:45 | Sydney Olympic U20 v Sutherland Sharks U20 | D | 1-1 |
| Australia New South Wales U20 League | 2022/07/31 02:45 | Sydney Olympic U20 v Blacktown City U20 | L | 1-3 |
| Australia New South Wales U20 League | 2022/07/27 09:00 | Sydney FC U20 v Sydney Olympic U20 | L | 5-0 |
| Australia New South Wales U20 League | 2022/07/24 05:30 | Mt Druitt Town Rangers U20 v Sydney Olympic U20 | D | 0-0 |
| Australia New South Wales U20 League | 2022/07/17 02:00 | Apia L Tigers U20 v Sydney Olympic U20 | D | 1-1 |
| Australia New South Wales U20 League | 2022/07/13 08:00 | Sydney Olympic U20 v Sydney United U20 | W | 6-0 |
| Australia New South Wales U20 League | 2022/07/09 03:45 | Sydney Olympic U20 v Sydney FC U20 | L | 0-2 |