| Australia New South Wales U20 League | 2023/02/26 01:45 | Sydney Olympic U20 v Rockdale Ilinden FC U20 | W | 2-5 |
| 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 | 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 | 2023/06/03 07:00 | Manly United U20 v Rockdale Ilinden FC U20 | D | 1-1 |
| Australia New South Wales U20 League | 2023/05/28 03:00 | Rockdale Ilinden FC U20 v Apia L Tigers U20 | W | 2-0 |
| Australia New South Wales U20 League | 2023/05/21 03:00 | Rockdale Ilinden FC U20 v St George City FA U20 | D | 0-0 |
| Australia New South Wales U20 League | 2023/05/14 03:00 | Blacktown City U20 v Rockdale Ilinden FC U20 | D | 1-1 |
| Australia New South Wales U20 League | 2023/05/07 03:00 | Rockdale Ilinden FC U20 v Sydney FC U20 | L | 1-4 |
| Australia New South Wales U20 League | 2023/04/29 09:48 | NWS Spirit FC U20 v Rockdale Ilinden FC U20 | L | 3-2 |
| Australia New South Wales U20 League | 2023/04/23 03:00 | Rockdale Ilinden FC U20 v Central Coast Mariners U20 | W | 1-0 |
| Australia New South Wales U20 League | 2023/04/15 06:45 | Marconi Stallions U20 v Rockdale Ilinden FC U20 | L | 2-1 |
| Australia New South Wales U20 League | 2023/05/27 06:30 | Sydney Olympic U20 v Manly United U20 | L | 0-3 |
| Australia New South Wales U20 League | 2023/05/20 06:10 | Sutherland Sharks U20 v Sydney Olympic U20 | L | 2-0 |
| Australia New South Wales U20 League | 2023/05/14 03:00 | Sydney United U20 v Sydney Olympic U20 | L | 4-1 |
| Australia New South Wales U20 League | 2023/05/06 06:30 | Sydney Olympic U20 v Marconi Stallions U20 | W | 3-2 |
| Australia New South Wales U20 League | 2023/04/29 06:30 | Sydney Olympic U20 v Wollongong Wolves U20 | L | 1-4 |
| Australia New South Wales U20 League | 2023/04/22 23:00 | Apia L Tigers U20 v Sydney Olympic U20 | W | 1-2 |
| Australia New South Wales U20 League | 2023/04/06 07:45 | Mt Druitt Town Rangers U20 v Sydney Olympic U20 | L | 3-1 |
| Australia New South Wales U20 League | 2023/04/01 05:30 | Sydney Olympic U20 v Bull FC Academy U20 | L | 0-3 |