Head to Head
| Australia New South Wales Premier League | 2021/03/28 07:30 | Sydney FC U21 v Sydney Olympic | W | 1-2 |
| Australia New South Wales Premier League | 2020/08/09 07:00 | Sydney Olympic v Sydney FC U21 | W | 2-0 |
| 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 | 2021/06/06 04:30 | Wollongong Wolves v Sydney Olympic | W | 1-5 |
| Australia New South Wales Premier League | 2021/05/30 07:30 | Apia L Tigers v Sydney Olympic | D | 1-1 |
| Australia FFA Cup Qualifying | 2021/05/26 09:00 | Liverpool Olympic Football Club v Sydney Olympic | W | 0-9 |
| Australia New South Wales Premier League | 2021/05/23 05:00 | Sydney Olympic v Rockdale Ilinden FC | D | 2-2 |
| Australia New South Wales Premier League | 2021/05/16 05:00 | Sydney United 58 v Sydney Olympic | L | 3-1 |
| Australia New South Wales Premier League | 2021/05/09 06:00 | Sydney Olympic v Blacktown City | L | 1-2 |
| Australia FFA Cup Qualifying | 2021/05/05 09:45 | Menai Hawks FC v Sydney Olympic | W | 1-3 |
| Australia New South Wales Premier League | 2021/05/01 05:30 | Sutherland Sharks v Sydney Olympic | W | 2-3 |
Away History
| Australia New South Wales Premier League | 2021/06/06 08:30 | Sydney FC U21 v Mt Druitt Town Rangers | W | 5-2 |
| Australia New South Wales Premier League | 2021/05/29 09:00 | Bulls FC Academy v Sydney FC U21 | D | 2-2 |
| Australia New South Wales Premier League | 2021/05/23 03:00 | Sydney FC U21 v Sydney United 58 | L | 1-5 |
| Australia New South Wales Premier League | 2021/05/16 08:30 | Sydney FC U21 v Marconi Stallions | D | 3-3 |
| Australia New South Wales Premier League | 2021/05/09 05:00 | Rockdale Ilinden FC v Sydney FC U21 | L | 4-1 |
| Australia New South Wales Premier League | 2021/05/02 08:30 | Sydney FC U21 v Wollongong Wolves | L | 3-5 |
| Australia New South Wales Premier League | 2021/04/25 05:00 | Blacktown City v Sydney FC U21 | L | 3-0 |
| Australia New South Wales Premier League | 2021/04/18 08:30 | Sydney FC U21 v Apia L Tigers | L | 2-3 |