| 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 | 2021/02/27 02:45 | Sydney Olympic U20 v Sydney United U20 | W | 3-0 |
| Australia New South Wales U20 League | 2020/08/02 03:00 | Sydney United U20 v Sydney Olympic U20 | W | 2-3 |
| Australia New South Wales U20 League | 2019/08/04 02:45 | Sydney Olympic U20 v Sydney United U20 | W | 3-0 |
| Australia New South Wales U20 League | 2019/05/12 05:06 | Sydney United U20 v Sydney Olympic U20 | L | 3-0 |
| Australia New South Wales U20 League | 2018/08/12 02:04 | Sydney Olympic U20 v Sydney United U20 | L | 0-4 |
| Australia New South Wales U20 League | 2018/05/19 07:34 | Sydney United U20 v Sydney Olympic U20 | L | 3-1 |
| Australia New South Wales U20 League | 2017/07/30 04:04 | Sydney United U20 v Sydney Olympic U20 | L | 6-1 |
| Australia New South Wales U20 League | 2021/06/20 03:45 | Sydney Olympic U20 v Mt Druitt Town Rangers U20 | W | 1-0 |
| 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 | 2021/06/06 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 | 2022/03/06 02:00 | Sydney United U20 v Wollongong Wolves U20 | L | 0-3 |
| Australia New South Wales U20 League | 2021/06/20 02:30 | Sydney United U20 v Bull FC Academy U20 | L | 1-2 |
| Australia New South Wales U20 League | 2021/06/13 02:45 | Sydney United U20 v Marconi Stallions U20 | W | 2-0 |
| Australia New South Wales U20 League | 2021/06/06 03:00 | Blacktown City U20 v Sydney United U20 | L | 6-2 |
| Australia New South Wales U20 League | 2021/05/30 02:49 | Sydney United U20 v Sutherland Sharks U20 | L | 1-7 |
| Australia New South Wales U20 League | 2021/05/16 02:30 | Sydney United U20 v Sydney Olympic U20 | L | 1-5 |
| Australia New South Wales U20 League | 2021/05/08 09:15 | Apia L Tigers U20 v Sydney United U20 | W | 0-2 |
| Australia New South Wales U20 League | 2021/05/02 02:30 | Sydney United U20 v Manly United U20 | W | 5-1 |