| Australia New South Wales U20 League | 2022/05/29 04:00 | Rockdale Ilinden FC U20 v Sydney Olympic U20 | D | 1-1 |
| Australia New South Wales U20 League | 2022/03/13 02:45 | Sydney Olympic U20 v Rockdale Ilinden FC U20 | W | 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 | W | 0-3 |
| Australia New South Wales U20 League | 2023/02/19 01:45 | Sydney FC U20 v Sydney Olympic U20 | L | 4-1 |
| Australia New South Wales U20 League | 2023/02/11 06:00 | Manly United U20 v Sydney Olympic U20 | D | 1-1 |
| Australia New South Wales U20 League | 2023/02/05 01:45 | Sydney Olympic U20 v Sutherland Sharks U20 | D | 1-1 |
| Australia New South Wales U20 League | 2022/07/31 02:45 | Sydney Olympic U20 v Blacktown City U20 | L | 1-3 |
| Australia New South Wales U20 League | 2022/07/27 09:00 | Sydney FC U20 v Sydney Olympic U20 | L | 5-0 |
| Australia New South Wales U20 League | 2022/07/24 05:30 | Mt Druitt Town Rangers U20 v Sydney Olympic U20 | D | 0-0 |
| Australia New South Wales U20 League | 2022/07/17 02:00 | Apia L Tigers U20 v Sydney Olympic U20 | D | 1-1 |
| Australia New South Wales U20 League | 2022/07/13 08:00 | Sydney Olympic U20 v Sydney United U20 | W | 6-0 |
| Australia New South Wales U20 League | 2023/02/19 02:00 | Rockdale Ilinden FC U20 v Manly United U20 | W | 1-0 |
| Australia New South Wales U20 League | 2023/02/12 04:00 | Apia L Tigers U20 v Rockdale Ilinden FC U20 | D | 1-1 |
| Australia New South Wales U20 League | 2023/02/04 06:00 | St George City FA U20 v Rockdale Ilinden FC U20 | W | 0-2 |
| Australia New South Wales U20 League | 2022/07/31 03:00 | Manly United U20 v Rockdale Ilinden FC U20 | L | 4-2 |
| Australia New South Wales U20 League | 2022/07/24 04:00 | Rockdale Ilinden FC U20 v Sydney FC U20 | L | 0-4 |
| Australia New South Wales U20 League | 2022/07/16 03:00 | Bull FC Academy U20 v Rockdale Ilinden FC U20 | W | 0-1 |
| Australia New South Wales U20 League | 2022/07/10 04:00 | Rockdale Ilinden FC U20 v Sutherland Sharks U20 | W | 3-1 |
| Australia New South Wales U20 League | 2022/07/01 07:30 | Wollongong Wolves U20 v Rockdale Ilinden FC U20 | L | 2-0 |