| Australia New South Wales U20 League | 2021/03/28 05:30 | Sydney FC U20 v Sydney Olympic U20 | L | 1-0 |
| Australia New South Wales U20 League | 2019/05/17 08:00 | Sydney Olympic U20 v Sydney FC U20 | L | 1-2 |
| Australia New South Wales U20 League | 2017/03/25 06:45 | Sydney FC 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 | 2021/05/30 01:00 | Apia L Tigers U20 v Sydney Olympic U20 | L | 2-0 |
| Australia New South Wales U20 League | 2021/05/23 02:45 | Sydney Olympic U20 v Rockdale Ilinden FC U20 | D | 0-0 |
| Australia New South Wales U20 League | 2021/05/16 02:30 | Sydney United U20 v Sydney Olympic U20 | W | 1-5 |
| Australia New South Wales U20 League | 2021/05/09 03:45 | Sydney Olympic U20 v Blacktown City U20 | D | 1-1 |
| 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 | 2021/04/25 03:45 | Sydney Olympic U20 v Bull FC Academy U20 | W | 2-1 |
| Australia New South Wales U20 League | 2021/04/17 06:00 | Marconi Stallions U20 v Sydney Olympic U20 | L | 2-0 |
| Australia New South Wales U20 League | 2021/05/29 07:00 | Bull FC Academy U20 v Sydney FC U20 | W | 0-3 |
| Australia New South Wales U20 League | 2021/05/02 06:30 | Sydney FC U20 v Wollongong Wolves U20 | W | 1-0 |
| Australia New South Wales U20 League | 2021/04/20 09:00 | Mt Druitt Town Rangers U20 v Sydney FC U20 | L | 3-2 |
| Australia New South Wales U20 League | 2021/04/18 06:30 | Sydney FC U20 v Apia L Tigers U20 | W | 3-0 |
| Australia New South Wales U20 League | 2021/04/02 06:00 | Manly United U20 v Sydney FC U20 | L | 1-0 |
| 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 | 2021/03/07 02:30 | Sydney United U20 v Sydney FC U20 | W | 1-3 |
| Australia New South Wales U20 League | 2021/02/26 06:45 | Marconi Stallions U20 v Sydney FC U20 | D | 0-0 |