| Australia New South Wales U20 League | 2022/07/31 02:45 | Sydney Olympic U20 v Blacktown City U20 | W | 1-3 |
| Australia New South Wales U20 League | 2022/05/15 03:00 | Blacktown City U20 v Sydney Olympic U20 | W | 3-1 |
| Australia New South Wales U20 League | 2021/05/09 03:45 | Sydney Olympic U20 v Blacktown City U20 | D | 1-1 |
| Australia Friendlies | 2021/02/06 06:00 | Blacktown City U20 v Sydney Olympic U20 | L | 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 | L | 3-1 |
| Australia New South Wales U20 League | 2018/07/01 03:06 | Blacktown City U20 v Sydney Olympic U20 | W | 3-1 |
| Australia New South Wales U20 League | 2023/03/11 05:45 | Marconi Stallions U20 v Blacktown City U20 | L | 2-0 |
| Australia New South Wales U20 League | 2023/03/05 02:00 | Blacktown City U20 v Mt Druitt Town Rangers U20 | W | 3-0 |
| Australia New South Wales U20 League | 2023/02/19 04:00 | Blacktown City U20 v NWS Spirit FC U20 | W | 2-0 |
| Australia New South Wales U20 League | 2023/02/10 06:30 | Western Sydney Wanderers U20 v Blacktown City U20 | L | 3-0 |
| Australia New South Wales U20 League | 2023/02/05 04:00 | Blacktown City U20 v Manly United U20 | W | 6-0 |
| Australia New South Wales U20 League | 2022/08/21 07:30 | Blacktown City U20 v Mt Druitt Town Rangers U20 | L | 1-2 |
| Australia New South Wales U20 League | 2022/08/14 03:15 | Blacktown City U20 v Sydney FC U20 | L | 0-2 |
| Australia New South Wales U20 League | 2022/07/31 02:45 | Sydney Olympic U20 v Blacktown City U20 | W | 1-3 |
| Australia New South Wales U20 League | 2023/03/11 06:00 | Western Sydney Wanderers U20 v Sydney Olympic U20 | L | 3-2 |
| Australia New South Wales U20 League | 2023/03/04 06:00 | St George City FA U20 v Sydney Olympic U20 | W | 0-1 |
| Australia New South Wales U20 League | 2023/02/26 01:45 | Sydney Olympic U20 v Rockdale Ilinden FC U20 | L | 2-5 |
| Australia New South Wales U20 League | 2023/02/19 01:45 | Sydney FC U20 v Sydney Olympic U20 | L | 4-1 |
| Australia New South Wales U20 League | 2023/02/11 06:00 | Manly United U20 v Sydney Olympic U20 | D | 1-1 |
| Australia New South Wales U20 League | 2023/02/05 01:45 | Sydney Olympic U20 v Sutherland Sharks U20 | D | 1-1 |
| Australia New South Wales U20 League | 2022/07/31 02:45 | Sydney Olympic U20 v Blacktown City U20 | L | 1-3 |
| Australia New South Wales U20 League | 2022/07/27 09:00 | Sydney FC U20 v Sydney Olympic U20 | L | 5-0 |