Head to Head
| Australia New South Wales Premier League | 2019/08/11 05:00 | Sydney FC U21 v Sydney Olympic | W | 1-3 |
| Australia New South Wales Premier League | 2019/05/17 10:00 | Sydney Olympic v Sydney FC U21 | L | 2-3 |
| Australia New South Wales Premier League | 2018/07/21 09:45 | Sydney FC U21 v Sydney Olympic | W | 2-3 |
| Australia New South Wales Premier League | 2018/04/29 05:00 | Sydney Olympic v Sydney FC U21 | W | 1-0 |
| Australia New South Wales Premier League | 2017/06/12 08:00 | Sydney Olympic v Sydney FC U21 | W | 2-0 |
| Australia New South Wales Premier League | 2017/03/25 08:45 | Sydney FC U21 v Sydney Olympic | W | 0-1 |
Home History
| Australia New South Wales Premier League | 2020/08/02 05:00 | Sydney United 58 v Sydney Olympic | W | 0-2 |
| Australia New South Wales Premier League | 2020/03/14 06:00 | Marconi Stallions v Sydney Olympic | L | 2-0 |
| Australia New South Wales Premier League | 2020/03/08 07:00 | Apia L Tigers v Sydney Olympic | L | 2-1 |
| Australia New South Wales Premier League | 2020/03/01 05:00 | Sydney Olympic v Wollongong Wolves | L | 1-2 |
| Australia Friendlies | 2020/02/15 05:35 | Sutherland Sharks v Sydney Olympic | W | 1-2 |
| Australia Friendlies | 2020/02/12 08:48 | Sydney Olympic v St George City FA | L | 2-3 |
| Australia Friendlies | 2020/02/05 09:03 | Bulls FC Academy v Sydney Olympic | W | 0-3 |
| Australia Friendlies | 2020/02/01 08:09 | Manly Utd v Sydney Olympic | L | 2-0 |
Away History
| Australia New South Wales Premier League | 2020/08/02 07:00 | Sydney FC U21 v Western Sydney Wanderers U21 | W | 3-2 |
| Australia New South Wales Premier League | 2020/03/15 04:00 | Bulls FC Academy v Sydney FC U21 | W | 0-4 |
| Australia New South Wales Premier League | 2020/03/08 07:30 | Sydney FC U21 v Marconi Stallions | L | 0-4 |
| Australia New South Wales Premier League | 2020/03/01 03:00 | Mt Druitt Town Rangers v Sydney FC U21 | W | 1-2 |
| Australia A-League Youth | 2020/01/31 05:30 | Sydney FC U21 v Melbourne Victory U21 | W | 5-1 |
| Australia A-League Youth | 2020/01/25 07:00 | Sydney FC U21 v Canberra United FC U21 | W | 7-0 |
| Australia A-League Youth | 2020/01/19 00:00 | Western Sydney Wanderers U21 v Sydney FC U21 | D | 1-1 |
| Australia A-League Youth | 2019/12/29 10:00 | Sydney FC U21 v Central Coast Mariners U21 | W | 5-3 |