| Australia New South Wales U20 League | 2023/02/19 01:45 | Sydney FC U20 v Sydney Olympic U20 | W | 4-1 |
| Australia New South Wales U20 League | 2022/07/27 09:00 | Sydney FC U20 v Sydney Olympic U20 | W | 5-0 |
| Australia New South Wales U20 League | 2022/07/09 03:45 | Sydney Olympic U20 v Sydney FC U20 | W | 0-2 |
| Australia New South Wales U20 League | 2021/06/12 05:15 | Sydney Olympic U20 v Sydney FC U20 | D | 0-0 |
| Australia New South Wales U20 League | 2021/03/28 05:30 | Sydney FC U20 v Sydney Olympic U20 | W | 1-0 |
| Australia New South Wales U20 League | 2019/05/17 08:00 | Sydney Olympic U20 v Sydney FC U20 | W | 1-2 |
| Australia New South Wales U20 League | 2017/03/25 06:45 | Sydney FC U20 v Sydney Olympic U20 | L | 1-2 |
| Australia New South Wales U20 League | 2024/05/12 03:00 | Rockdale Ilinden FC U20 v Sydney FC U20 | L | 5-0 |
| Australia New South Wales U20 League | 2024/05/05 09:30 | Sydney FC U20 v Apia L Tigers U20 | W | 6-1 |
| Australia New South Wales U20 League | 2024/04/26 07:30 | Sydney FC U20 v Sydney United U20 | L | 2-3 |
| Australia New South Wales U20 League | 2024/04/07 02:00 | Blacktown City U20 v Sydney FC U20 | L | 4-0 |
| Australia New South Wales U20 League | 2024/03/29 06:30 | Sydney FC U20 v St George City FA U20 | L | 3-5 |
| Australia New South Wales U20 League | 2024/03/15 06:30 | Sydney FC U20 v Western Sydney Wanderers U20 | W | 3-0 |
| Australia New South Wales U20 League | 2024/02/23 06:30 | Sydney FC U20 v Manly United U20 | L | 0-1 |
| Australia New South Wales U20 League | 2023/07/28 07:30 | Sydney FC U20 v NWS Spirit FC U20 | W | 5-1 |
| Australia New South Wales U20 League | 2024/05/05 05:00 | St George Saints U20 v Sydney Olympic U20 | L | 4-3 |
| Australia New South Wales U20 League | 2024/04/21 03:00 | Sydney Olympic U20 v NWS Spirit FC U20 | W | 5-3 |
| Australia New South Wales U20 League | 2024/04/14 02:30 | Rockdale Ilinden FC U20 v Sydney Olympic U20 | L | 3-2 |
| Australia New South Wales U20 League | 2024/03/30 08:00 | Sydney Olympic U20 v Wollongong Wolves U20 | W | 5-2 |
| Australia New South Wales U20 League | 2024/03/22 06:30 | Manly United U20 v Sydney Olympic U20 | L | 2-0 |
| Australia New South Wales U20 League | 2024/03/16 09:00 | Apia L Tigers U20 v Sydney Olympic U20 | L | 1-0 |
| Australia New South Wales U20 League | 2024/03/09 07:40 | Sutherland Sharks U20 v Sydney Olympic U20 | L | 3-0 |
| Australia New South Wales U20 League | 2024/03/05 08:00 | Sydney Olympic U20 v Marconi Stallions U20 | W | 1-0 |