Head to Head
| Australia New South Wales Premier League | 2019/05/17 10:00 | Sydney Olympic v Sydney FC U21 | W | 2-3 |
| Australia New South Wales Premier League | 2018/07/21 09:45 | Sydney FC U21 v Sydney Olympic | L | 2-3 |
| Australia New South Wales Premier League | 2018/04/29 05:00 | Sydney Olympic v Sydney FC U21 | L | 1-0 |
| Australia New South Wales Premier League | 2017/06/12 08:00 | Sydney Olympic v Sydney FC U21 | L | 2-0 |
| Australia New South Wales Premier League | 2017/03/25 08:45 | Sydney FC U21 v Sydney Olympic | L | 0-1 |
Home History
| Australia New South Wales Premier League | 2019/08/03 09:00 | Sydney FC U21 v Sutherland Sharks | L | 0-4 |
| Australia New South Wales Premier League | 2019/07/27 09:00 | Apia L Tigers v Sydney FC U21 | D | 2-2 |
| Australia New South Wales Premier League | 2019/07/21 05:00 | Sydney United 58 v Sydney FC U21 | W | 0-2 |
| Australia New South Wales Premier League | 2019/07/06 09:00 | Sydney FC U21 v Rockdale Ilinden FC | W | 3-1 |
| Australia New South Wales Premier League | 2019/06/30 05:00 | Blacktown City v Sydney FC U21 | L | 3-1 |
| Australia New South Wales Premier League | 2019/06/22 09:00 | Sydney FC U21 v Mt Druitt Town Rangers | L | 3-5 |
| Australia New South Wales Premier League | 2019/06/16 05:00 | Wollongong Wolves v Sydney FC U21 | L | 4-0 |
| Australia New South Wales Premier League | 2019/06/09 05:00 | Marconi Stallions v Sydney FC U21 | L | 5-2 |
Away History
| Australia New South Wales Premier League | 2019/08/04 06:00 | Sydney Olympic v Sydney United 58 | W | 2-1 |
| Australia New South Wales Premier League | 2019/07/28 06:00 | Sydney Olympic v Marconi Stallions | L | 0-1 |
| Australia New South Wales Premier League | 2019/07/21 05:30 | Apia L Tigers v Sydney Olympic | L | 3-1 |
| Australia New South Wales Premier League | 2019/07/07 05:00 | Manly Utd v Sydney Olympic | W | 1-2 |
| Australia New South Wales Premier League | 2019/06/30 06:00 | Sydney Olympic v Rockdale Ilinden FC | W | 1-0 |
| Australia New South Wales Premier League | 2019/06/23 05:00 | Wollongong Wolves v Sydney Olympic | L | 2-0 |
| Australia New South Wales Premier League | 2019/06/16 08:15 | Sydney Olympic v Hakoah Sydney City East | W | 1-0 |
| Australia New South Wales Premier League | 2019/06/09 05:00 | Blacktown City v Sydney Olympic | D | 1-1 |