| 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 | 2018/07/08 05:00 | Rockdale City Suns U20 v Sydney Olympic U20 | W | 1-2 |
| Australia New South Wales U20 League | 2018/04/22 02:40 | Sydney Olympic U20 v Rockdale City Suns U20 | D | 1-1 |
| Australia New South Wales U20 League | 2017/06/25 02:45 | Sydney Olympic U20 v Rockdale City Suns U20 | L | 1-2 |
| Australia New South Wales U20 League | 2017/04/09 02:00 | Rockdale City Suns U20 v Sydney Olympic U20 | D | 0-0 |
| Australia New South Wales U20 League | 2019/06/26 10:02 | Sydney Olympic U20 v Hakoah Sydney City East U20 | W | 2-1 |
| 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 | 2019/06/23 04:25 | Rockdale City Suns U20 v Apia L Tigers U20 | D | 2-2 |
| Australia New South Wales U20 League | 2019/06/15 07:07 | Mt Druitt Town Rangers U20 v Rockdale City Suns U20 | W | 5-7 |
| Australia New South Wales U20 League | 2019/06/09 05:03 | Hakoah Sydney City East U20 v Rockdale City Suns U20 | L | 3-2 |
| Australia New South Wales U20 League | 2019/06/02 04:33 | Rockdale City Suns U20 v Marconi Stallions U20 | L | 1-2 |
| Australia New South Wales U20 League | 2019/05/26 03:05 | Rockdale City Suns U20 v Sydney United U20 | D | 3-3 |
| Australia New South Wales U20 League | 2019/05/18 06:33 | Sutherland Sharks U20 v Rockdale City Suns U20 | W | 0-1 |
| Australia New South Wales U20 League | 2019/05/11 06:02 | Wollongong Wolves U20 v Rockdale City Suns U20 | W | 0-2 |
| Australia New South Wales U20 League | 2019/05/05 04:33 | Rockdale City Suns U20 v Manly United U20 | L | 2-3 |