| Australia New South Wales U20 League | 2022/03/13 02:45 | Sydney Olympic U20 v Rockdale Ilinden FC U20 | L | 2-1 |
| Australia New South Wales U20 League | 2021/05/23 02:45 | Sydney Olympic U20 v Rockdale Ilinden FC U20 | D | 0-0 |
| Australia New South Wales U20 League | 2021/03/07 02:00 | Rockdale Ilinden FC U20 v Sydney Olympic U20 | L | 0-3 |
| Australia New South Wales U20 League | 2022/05/22 04:00 | Rockdale Ilinden FC U20 v Blacktown City U20 | L | 0-3 |
| Australia New South Wales U20 League | 2022/05/15 04:00 | Rockdale Ilinden FC U20 v Manly United U20 | L | 2-5 |
| Australia New South Wales U20 League | 2022/05/08 06:30 | Sydney FC U20 v Rockdale Ilinden FC U20 | L | 3-0 |
| Australia New South Wales U20 League | 2022/05/01 04:00 | Rockdale Ilinden FC U20 v Bull FC Academy U20 | D | 1-1 |
| Australia New South Wales U20 League | 2022/04/23 03:30 | Sutherland Sharks U20 v Rockdale Ilinden FC U20 | W | 0-2 |
| Australia New South Wales U20 League | 2022/04/17 04:00 | Rockdale Ilinden FC U20 v Wollongong Wolves U20 | L | 0-3 |
| Australia New South Wales U20 League | 2022/04/10 03:00 | Sydney United U20 v Rockdale Ilinden FC U20 | W | 1-4 |
| Australia New South Wales U20 League | 2022/04/03 04:00 | Rockdale Ilinden FC U20 v Mt Druitt Town Rangers U20 | D | 3-3 |
| Australia New South Wales U20 League | 2022/05/21 07:00 | Manly United U20 v Sydney Olympic U20 | L | 2-1 |
| Australia New South Wales U20 League | 2022/05/15 03:00 | Blacktown City U20 v Sydney Olympic U20 | L | 3-1 |
| Australia New South Wales U20 League | 2022/05/10 09:30 | Marconi Stallions U20 v Sydney Olympic U20 | W | 1-2 |
| Australia New South Wales U20 League | 2022/05/07 09:00 | Sydney Olympic U20 v Mt Druitt Town Rangers U20 | W | 3-1 |
| Australia New South Wales U20 League | 2022/05/01 01:00 | Sydney Olympic U20 v Apia L Tigers U20 | W | 2-0 |
| Australia New South Wales U20 League | 2022/04/27 07:30 | Wollongong Wolves U20 v Sydney Olympic U20 | W | 1-2 |
| Australia New South Wales U20 League | 2022/04/18 03:00 | Sydney United U20 v Sydney Olympic U20 | W | 0-2 |
| Australia New South Wales U20 League | 2022/04/09 03:30 | Sutherland Sharks U20 v Sydney Olympic U20 | L | 2-0 |