| Australia New South Wales U20 League | 2023/07/01 04:00 | Sydney Olympic U20 v Blacktown City U20 | L | 0-2 |
| Australia New South Wales U20 League | 2023/03/19 06:00 | Blacktown City U20 v Sydney Olympic U20 | W | 1-3 |
| 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 | 2022/05/15 03:00 | Blacktown City U20 v Sydney Olympic U20 | L | 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 | 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 | 2024/04/21 03:00 | Sydney Olympic U20 v NWS Spirit FC U20 | W | 5-3 |
| Australia New South Wales U20 League | 2024/04/14 02:30 | Rockdale Ilinden FC U20 v Sydney Olympic U20 | L | 3-2 |
| Australia New South Wales U20 League | 2024/03/30 08:00 | Sydney Olympic U20 v Wollongong Wolves U20 | W | 5-2 |
| Australia New South Wales U20 League | 2024/03/22 06:30 | Manly United U20 v Sydney Olympic U20 | L | 2-0 |
| Australia New South Wales U20 League | 2024/03/16 09:00 | Apia L Tigers U20 v Sydney Olympic U20 | L | 1-0 |
| Australia New South Wales U20 League | 2024/03/09 07:40 | Sutherland Sharks U20 v Sydney Olympic U20 | L | 3-0 |
| Australia New South Wales U20 League | 2024/03/05 08:00 | Sydney Olympic U20 v Marconi Stallions U20 | W | 1-0 |
| Australia New South Wales U20 League | 2024/03/02 08:00 | Sydney Olympic U20 v Sydney United U20 | W | 3-0 |
| Australia New South Wales U20 League | 2024/04/07 02:00 | Blacktown City U20 v Sydney FC U20 | W | 4-0 |
| Australia New South Wales U20 League | 2024/03/31 02:00 | Blacktown City U20 v Sydney United U20 | W | 2-1 |
| Australia New South Wales U20 League | 2024/03/23 06:00 | St George City FA U20 v Blacktown City U20 | L | 3-1 |
| Australia New South Wales U20 League | 2024/03/17 02:00 | Rockdale Ilinden FC U20 v Blacktown City U20 | L | 1-0 |
| Australia New South Wales U20 League | 2024/03/10 02:00 | Blacktown City U20 v Wollongong Wolves U20 | W | 5-2 |
| Australia New South Wales U20 League | 2024/03/05 08:30 | Manly United U20 v Blacktown City U20 | L | 6-1 |
| Australia New South Wales U20 League | 2024/03/02 06:00 | Blacktown City U20 v Sutherland Sharks U20 | L | 1-2 |
| Australia New South Wales U20 League | 2024/02/24 06:00 | St George Saints U20 v Blacktown City U20 | L | 2-1 |