| Australia New South Wales U20 League | 2017/03/25 06:45 | Sydney FC U20 v Sydney Olympic U20 | W | 1-2 |
| Australia New South Wales U20 League | 2019/05/12 05:06 | Sydney United U20 v Sydney Olympic U20 | L | 3-0 |
| Australia New South Wales U20 League | 2019/05/04 07:02 | Marconi Stallions U20 v Sydney Olympic U20 | D | 1-1 |
| Australia New South Wales U20 League | 2019/04/25 04:32 | Sydney Olympic U20 v Apia L Tigers U20 | L | 0-2 |
| Australia New South Wales U20 League | 2019/04/19 04:35 | Sydney Olympic U20 v Manly United U20 | W | 3-1 |
| Australia New South Wales U20 League | 2019/04/14 04:31 | Rockdale City Suns U20 v Sydney Olympic U20 | L | 3-0 |
| Australia New South Wales U20 League | 2019/04/09 09:36 | Mt Druitt Town Rangers U20 v Sydney Olympic U20 | D | 1-1 |
| Australia New South Wales U20 League | 2019/04/07 03:56 | Sydney Olympic U20 v Wollongong Wolves U20 | W | 1-0 |
| Australia New South Wales U20 League | 2019/03/31 03:00 | Hakoah Sydney City East U20 v Sydney Olympic U20 | W | 2-3 |
| Australia New South Wales U20 League | 2019/04/21 04:30 | Rockdale City Suns U20 v Sydney FC U20 | D | 1-1 |
| Australia New South Wales U20 League | 2019/03/23 06:00 | Sydney FC U20 v Marconi Stallions U20 | D | 0-0 |
| Australia New South Wales U20 League | 2018/09/09 02:30 | Sydney FC U20 v Sutherland Sharks U20 | L | 3-5 |
| Australia New South Wales U20 League | 2017/09/02 04:30 | Sydney FC U20 v Apia L Tigers U20 | L | 1-2 |
| Australia New South Wales U20 League | 2017/06/18 07:45 | Sydney FC U20 v Manly United U20 | W | 4-2 |
| Australia New South Wales U20 League | 2017/05/13 07:00 | Bonnyrigg White Eagles U20 v Sydney FC U20 | W | 0-6 |
| Australia New South Wales U20 League | 2017/03/25 06:45 | Sydney FC U20 v Sydney Olympic U20 | L | 1-2 |