| Australia New South Wales U20 League | 2021/02/27 02:45 | Sydney Olympic U20 v Sydney United U20 | L | 3-0 |
| Australia New South Wales U20 League | 2020/08/02 03:00 | Sydney United U20 v Sydney Olympic U20 | L | 2-3 |
| Australia New South Wales U20 League | 2019/08/04 02:45 | Sydney Olympic U20 v Sydney United U20 | L | 3-0 |
| Australia New South Wales U20 League | 2019/05/12 05:06 | Sydney United U20 v Sydney Olympic U20 | W | 3-0 |
| Australia New South Wales U20 League | 2018/08/12 02:04 | Sydney Olympic U20 v Sydney United U20 | W | 0-4 |
| Australia New South Wales U20 League | 2018/05/19 07:34 | Sydney United U20 v Sydney Olympic U20 | W | 3-1 |
| Australia New South Wales U20 League | 2017/07/30 04:04 | Sydney United U20 v Sydney Olympic U20 | W | 6-1 |
| Australia New South Wales U20 League | 2017/05/07 02:52 | Sydney Olympic U20 v Sydney United U20 | L | 2-0 |
| Australia New South Wales U20 League | 2021/03/21 02:30 | Sydney United U20 v Blacktown City U20 | D | 1-1 |
| Australia New South Wales U20 League | 2021/03/13 02:30 | Sutherland Sharks U20 v Sydney United U20 | L | 2-0 |
| Australia New South Wales U20 League | 2021/03/07 02:30 | Sydney United U20 v Sydney FC U20 | L | 1-3 |
| Australia New South Wales U20 League | 2021/02/27 02:45 | Sydney Olympic U20 v Sydney United U20 | L | 3-0 |
| Australia Friendlies | 2021/02/06 06:00 | Sydney United U20 v Bull FC Academy U20 | L | 0-1 |
| Australia New South Wales U20 League | 2020/10/10 06:00 | Apia L Tigers U20 v Sydney United U20 | W | 1-2 |
| Australia New South Wales U20 League | 2020/10/04 02:00 | Sydney United U20 v Rockdale City Suns U20 | L | 2-3 |
| Australia New South Wales U20 League | 2020/09/25 07:30 | Blacktown City U20 v Sydney United U20 | L | 2-1 |
| Australia New South Wales U20 League | 2021/03/13 02:45 | Sydney Olympic U20 v Apia L Tigers U20 | W | 2-1 |
| Australia New South Wales U20 League | 2021/03/07 02:00 | Rockdale Ilinden FC U20 v Sydney Olympic U20 | W | 0-3 |
| Australia New South Wales U20 League | 2021/02/27 02:45 | Sydney Olympic U20 v Sydney United U20 | W | 3-0 |
| Australia Friendlies | 2021/02/06 06:00 | Blacktown City U20 v Sydney Olympic U20 | W | 0-3 |
| Australia New South Wales U20 League | 2020/10/10 06:00 | Mt Druitt Town Rangers U20 v Sydney Olympic U20 | W | 4-5 |
| Australia New South Wales U20 League | 2020/10/03 07:00 | Sydney Olympic U20 v Western Sydney Wanderers U20 | L | 0-3 |
| Australia New South Wales U20 League | 2020/09/26 07:00 | Sydney Olympic U20 v North Shore Mariners U20 | W | 1-0 |
| Australia New South Wales U20 League | 2020/09/20 02:30 | Wollongong Wolves U20 v Sydney Olympic U20 | D | 1-1 |