| 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 | 2018/04/15 02:48 | Sydney Olympic U20 v Blacktown City U20 | W | 1-5 |
| Australia New South Wales U20 League | 2017/07/16 03:00 | Blacktown City U20 v Sydney Olympic U20 | W | 3-0 |
| Australia New South Wales U20 League | 2017/04/23 02:49 | Sydney Olympic U20 v Blacktown City U20 | W | 1-6 |
| Australia Friendlies | 2017/03/05 05:00 | Blacktown City U20 v Sydney Olympic U20 | W | 2-0 |
| Australia Friendlies | 2021/01/16 00:00 | Hills United FC U20 v Blacktown City U20 | W | 0-2 |
| Australia New South Wales U20 League | 2020/10/25 02:00 | Sydney FC U20 v Blacktown City U20 | W | 1-2 |
| Australia New South Wales U20 League | 2020/10/17 05:30 | Blacktown City U20 v Western Sydney Wanderers U20 | W | 3-1 |
| Australia New South Wales U20 League | 2020/10/09 06:30 | Blacktown City U20 v Western Sydney Wanderers U20 | W | 6-2 |
| Australia New South Wales U20 League | 2020/10/02 07:30 | Blacktown City U20 v Apia L Tigers U20 | W | 4-3 |
| Australia New South Wales U20 League | 2020/09/25 07:30 | Blacktown City U20 v Sydney United U20 | W | 2-1 |
| Australia New South Wales U20 League | 2020/09/19 07:00 | Manly United U20 v Blacktown City U20 | W | 1-2 |
| Australia New South Wales U20 League | 2020/09/11 07:30 | Blacktown City U20 v Sydney FC U20 | W | 2-0 |
| Australia New South Wales U20 League | 2020/10/10 06:00 | Mt Druitt Town Rangers U20 v Sydney Olympic U20 | W | 4-5 |
| Australia New South Wales U20 League | 2020/10/03 07:00 | Sydney Olympic U20 v Western Sydney Wanderers U20 | L | 0-3 |
| Australia New South Wales U20 League | 2020/09/26 07:00 | Sydney Olympic U20 v North Shore Mariners U20 | W | 1-0 |
| Australia New South Wales U20 League | 2020/09/20 02:30 | Wollongong Wolves U20 v Sydney Olympic U20 | D | 1-1 |
| Australia New South Wales U20 League | 2020/09/13 03:00 | Sydney Olympic U20 v Apia L Tigers U20 | W | 4-0 |
| Australia New South Wales U20 League | 2020/09/05 04:00 | Marconi Stallions U20 v Sydney Olympic U20 | D | 1-1 |
| Australia New South Wales U20 League | 2020/08/30 06:55 | Sydney Olympic U20 v Rockdale City Suns U20 | L | 0-2 |
| Australia New South Wales U20 League | 2020/08/21 07:45 | Manly United U20 v Sydney Olympic U20 | D | 1-1 |