Head to Head
| Australia New South Wales Premier League | 2024/05/17 09:30 | Sydney FC U21 v Sydney Olympic | W | 1-3 |
| Australia New South Wales Premier League | 2023/06/04 06:00 | Sydney Olympic v Sydney FC U21 | L | 1-2 |
| Australia New South Wales Premier League | 2023/02/19 04:00 | Sydney FC U21 v Sydney Olympic | W | 2-3 |
| Australia New South Wales Premier League | 2022/07/09 06:00 | Sydney Olympic v Sydney FC U21 | L | 0-3 |
| Australia New South Wales Premier League | 2022/04/24 06:30 | Sydney FC U21 v Sydney Olympic | L | 3-1 |
| Australia New South Wales Premier League | 2021/06/12 07:30 | Sydney Olympic v Sydney FC U21 | W | 1-0 |
| 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 |