| 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 | 2019/03/24 02:49 | Sydney Olympic U20 v Blacktown City U20 | W | 3-1 |
| Australia New South Wales U20 League | 2023/06/18 07:30 | Sydney Olympic U20 v St George City FA U20 | W | 1-0 |
| Australia New South Wales U20 League | 2023/06/11 03:00 | Rockdale Ilinden FC U20 v Sydney Olympic U20 | D | 2-2 |
| Australia New South Wales U20 League | 2023/05/27 06:30 | Sydney Olympic U20 v Manly United U20 | L | 0-3 |
| Australia New South Wales U20 League | 2023/05/20 06:10 | Sutherland Sharks U20 v Sydney Olympic U20 | L | 2-0 |
| Australia New South Wales U20 League | 2023/05/14 03:00 | Sydney United U20 v Sydney Olympic U20 | L | 4-1 |
| Australia New South Wales U20 League | 2023/05/06 06:30 | Sydney Olympic U20 v Marconi Stallions U20 | W | 3-2 |
| Australia New South Wales U20 League | 2023/04/29 06:30 | Sydney Olympic U20 v Wollongong Wolves U20 | L | 1-4 |
| Australia New South Wales U20 League | 2023/04/22 23:00 | Apia L Tigers U20 v Sydney Olympic U20 | W | 1-2 |
| Australia New South Wales U20 League | 2023/06/25 03:00 | Blacktown City U20 v Marconi Stallions U20 | W | 3-1 |
| Australia New South Wales U20 League | 2023/06/17 07:00 | Mt Druitt Town Rangers U20 v Blacktown City U20 | L | 3-2 |
| Australia New South Wales U20 League | 2023/06/11 03:00 | Blacktown City U20 v Central Coast Mariners U20 | L | 1-3 |
| Australia New South Wales U20 League | 2023/06/03 09:30 | NWS Spirit FC U20 v Blacktown City U20 | L | 1-0 |
| Australia New South Wales U20 League | 2023/05/28 03:00 | Blacktown City U20 v Western Sydney Wanderers U20 | W | 3-1 |
| Australia New South Wales U20 League | 2023/05/20 09:15 | Manly United U20 v Blacktown City U20 | L | 3-1 |
| Australia New South Wales U20 League | 2023/05/14 03:00 | Blacktown City U20 v Rockdale Ilinden FC U20 | D | 1-1 |
| Australia New South Wales U20 League | 2023/05/05 07:30 | Wollongong Wolves U20 v Blacktown City U20 | D | 1-1 |