| 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 | 2018/06/16 04:35 | Hakoah Sydney City East U20 v Sydney Olympic U20 | L | 1-0 |
| Australia New South Wales U20 League | 2018/03/30 02:48 | Sydney Olympic U20 v Hakoah Sydney City East U20 | W | 3-0 |
| Australia New South Wales U20 League | 2017/08/06 05:00 | Sydney Olympic U20 v Hakoah Sydney City East U20 | L | 0-4 |
| Australia New South Wales U20 League | 2017/05/14 02:59 | Hakoah Sydney City East U20 v Sydney Olympic U20 | W | 0-1 |
| Australia New South Wales U20 League | 2019/06/23 03:03 | Wollongong Wolves U20 v Sydney Olympic U20 | D | 1-1 |
| 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 | 2019/06/02 03:47 | Sydney Olympic U20 v Mt Druitt Town Rangers U20 | W | 2-1 |
| Australia New South Wales U20 League | 2019/05/25 06:33 | Sutherland Sharks U20 v Sydney Olympic U20 | L | 1-0 |
| Australia New South Wales U20 League | 2019/05/17 08:00 | Sydney Olympic U20 v Sydney FC U20 | L | 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 | 2019/06/23 05:03 | Hakoah Sydney City East U20 v Marconi Stallions U20 | L | 0-1 |
| Australia New South Wales U20 League | 2019/06/09 05:03 | Hakoah Sydney City East U20 v Rockdale City Suns U20 | W | 3-2 |
| Australia New South Wales U20 League | 2019/06/02 05:03 | Hakoah Sydney City East U20 v Sutherland Sharks U20 | L | 0-3 |
| Australia New South Wales U20 League | 2019/05/19 03:04 | Blacktown City U20 v Hakoah Sydney City East U20 | L | 5-0 |
| Australia New South Wales U20 League | 2019/05/12 05:00 | Hakoah Sydney City East U20 v Mt Druitt Town Rangers U20 | W | 4-2 |
| Australia New South Wales U20 League | 2019/05/05 05:06 | Sydney United U20 v Hakoah Sydney City East U20 | W | 0-2 |
| Australia New South Wales U20 League | 2019/04/28 03:02 | Manly United U20 v Hakoah Sydney City East U20 | D | 2-2 |
| Australia New South Wales U20 League | 2019/04/21 05:00 | Hakoah Sydney City East U20 v Wollongong Wolves U20 | L | 1-3 |