| 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 | 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 | 2022/07/27 09:00 | Sydney FC U20 v Sydney Olympic U20 | L | 5-0 |
| Australia New South Wales U20 League | 2022/07/24 05:30 | Mt Druitt Town Rangers U20 v Sydney Olympic U20 | D | 0-0 |
| Australia New South Wales U20 League | 2022/07/17 02:00 | Apia L Tigers U20 v Sydney Olympic U20 | D | 1-1 |
| Australia New South Wales U20 League | 2022/07/13 08:00 | Sydney Olympic U20 v Sydney United U20 | W | 6-0 |
| Australia New South Wales U20 League | 2022/07/09 03:45 | Sydney Olympic U20 v Sydney FC U20 | L | 0-2 |
| Australia New South Wales U20 League | 2022/06/30 09:30 | Sydney Olympic U20 v Manly United U20 | W | 3-1 |
| Australia New South Wales U20 League | 2022/06/26 03:45 | Sydney Olympic U20 v Sutherland Sharks U20 | W | 4-1 |
| Australia New South Wales U20 League | 2022/06/19 03:45 | Sydney Olympic U20 v Marconi Stallions U20 | L | 1-2 |
| Australia New South Wales U20 League | 2022/07/24 03:00 | Blacktown City U20 v Wollongong Wolves U20 | W | 1-0 |
| Australia New South Wales U20 League | 2022/07/16 03:30 | Sutherland Sharks U20 v Blacktown City U20 | W | 0-5 |
| Australia New South Wales U20 League | 2022/07/09 03:00 | Manly United U20 v Blacktown City U20 | W | 1-4 |
| Australia New South Wales U20 League | 2022/07/03 06:30 | Sydney FC U20 v Blacktown City U20 | D | 1-1 |
| Australia New South Wales U20 League | 2022/06/29 09:45 | Blacktown City U20 v Sydney FC U20 | W | 3-2 |
| Australia New South Wales U20 League | 2022/06/26 03:00 | Blacktown City U20 v Bull FC Academy U20 | W | 4-0 |
| Australia New South Wales U20 League | 2022/06/19 07:00 | Sydney United U20 v Blacktown City U20 | W | 1-5 |
| Australia New South Wales U20 League | 2022/06/12 03:00 | Blacktown City U20 v Apia L Tigers U20 | W | 4-1 |