| 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 | 2022/07/24 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 | 2022/06/29 09:45 | Blacktown City U20 v Sydney FC U20 | L | 3-2 |
| Australia New South Wales U20 League | 2022/06/25 09:30 | Apia L Tigers U20 v Sydney FC U20 | W | 1-4 |
| Australia New South Wales U20 League | 2022/06/19 06:30 | Sydney FC U20 v Sutherland Sharks U20 | W | 2-0 |
| Australia New South Wales U20 League | 2022/06/10 07:00 | Manly United U20 v Sydney FC U20 | W | 1-3 |
| 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 |
| 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 | 2022/06/26 03:45 | Sydney Olympic U20 v Sutherland Sharks U20 | W | 4-1 |
| Australia New South Wales U20 League | 2022/06/19 03:45 | Sydney Olympic U20 v Marconi Stallions U20 | L | 1-2 |
| Australia New South Wales U20 League | 2022/06/13 03:45 | Sydney Olympic U20 v Wollongong Wolves U20 | D | 1-1 |