| Australia New South Wales U20 League | 2021/02/28 02:00 | Rockdale Ilinden FC U20 v Wollongong Wolves U20 | L | 2-3 |
| Australia New South Wales U20 League | 2020/09/27 03:00 | Rockdale Ilinden FC U20 v Apia L Tigers U20 | W | 3-1 |
| Australia New South Wales U20 League | 2020/09/20 06:30 | Rockdale Ilinden FC U20 v Sydney FC U20 | W | 2-0 |
| Australia New South Wales U20 League | 2021/02/27 02:45 | Sydney Olympic U20 v Sydney United U20 | W | 3-0 |
| Australia Friendlies | 2021/02/06 06:00 | Blacktown City U20 v Sydney Olympic U20 | W | 0-3 |
| Australia New South Wales U20 League | 2020/10/10 06:00 | Mt Druitt Town Rangers U20 v Sydney Olympic U20 | W | 4-5 |
| Australia New South Wales U20 League | 2020/10/03 07:00 | Sydney Olympic U20 v Western Sydney Wanderers U20 | L | 0-3 |
| Australia New South Wales U20 League | 2020/09/26 07:00 | Sydney Olympic U20 v North Shore Mariners U20 | W | 1-0 |
| Australia New South Wales U20 League | 2020/09/20 02:30 | Wollongong Wolves U20 v Sydney Olympic U20 | D | 1-1 |
| Australia New South Wales U20 League | 2020/09/13 03:00 | Sydney Olympic U20 v Apia L Tigers U20 | W | 4-0 |
| Australia New South Wales U20 League | 2020/09/05 04:00 | Marconi Stallions U20 v Sydney Olympic U20 | D | 1-1 |