| Australia Friendlies | 2021/02/06 06:00 | Blacktown City U20 v Sydney Olympic U20 | W | 0-3 |
| Australia New South Wales U20 League | 2020/08/14 07:30 | Blacktown City U20 v Sydney Olympic U20 | D | 3-3 |
| Australia New South Wales U20 League | 2019/06/09 03:03 | Blacktown City U20 v Sydney Olympic U20 | D | 1-1 |
| Australia New South Wales U20 League | 2019/03/24 02:49 | Sydney Olympic U20 v Blacktown City U20 | W | 3-1 |
| Australia New South Wales U20 League | 2018/07/01 03:06 | Blacktown City U20 v Sydney Olympic U20 | L | 3-1 |
| Australia New South Wales U20 League | 2018/04/15 02:48 | Sydney Olympic U20 v Blacktown City U20 | L | 1-5 |
| Australia New South Wales U20 League | 2017/07/16 03:00 | Blacktown City U20 v Sydney Olympic U20 | L | 3-0 |
| Australia New South Wales U20 League | 2017/04/23 02:49 | Sydney Olympic U20 v Blacktown City U20 | L | 1-6 |
| 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 | 2021/04/10 07:00 | Manly United U20 v Sydney Olympic U20 | L | 1-0 |
| Australia New South Wales U20 League | 2021/04/06 08:45 | Sydney Olympic U20 v Wollongong Wolves U20 | W | 4-1 |
| Australia New South Wales U20 League | 2021/04/03 06:00 | Mt Druitt Town Rangers U20 v Sydney Olympic U20 | W | 3-4 |
| 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 | 2021/03/13 02:45 | Sydney Olympic U20 v Apia L Tigers U20 | W | 2-1 |
| Australia New South Wales U20 League | 2021/05/01 06:00 | Marconi Stallions U20 v Blacktown City U20 | W | 1-2 |
| Australia New South Wales U20 League | 2021/04/11 03:00 | Blacktown City U20 v Mt Druitt Town Rangers U20 | W | 3-1 |
| Australia New South Wales U20 League | 2021/04/03 02:30 | Sutherland Sharks U20 v Blacktown City U20 | W | 0-8 |
| Australia New South Wales U20 League | 2021/03/28 02:00 | Blacktown City U20 v Rockdale Ilinden FC U20 | W | 3-0 |
| 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 06:00 | Manly United U20 v Blacktown City U20 | W | 0-1 |
| Australia New South Wales U20 League | 2021/03/07 02:00 | Blacktown City U20 v Bull FC Academy U20 | L | 2-3 |
| Australia New South Wales U20 League | 2021/02/27 06:00 | Blacktown City U20 v Apia L Tigers U20 | L | 1-2 |