| Australia New South Wales U20 League | 2023/06/11 03:00 | Rockdale Ilinden FC U20 v Sydney Olympic U20 | D | 2-2 |
| 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 | 2024/04/07 03:00 | Sydney United U20 v Rockdale Ilinden FC U20 | D | 2-2 |
| Australia New South Wales U20 League | 2024/03/31 02:00 | Rockdale Ilinden FC U20 v NWS Spirit FC U20 | W | 5-3 |
| Australia New South Wales U20 League | 2024/03/23 06:00 | Hills United FC U20 v Rockdale Ilinden FC U20 | W | 2-3 |
| Australia New South Wales U20 League | 2024/03/17 02:00 | Rockdale Ilinden FC U20 v Blacktown City U20 | W | 1-0 |
| Australia New South Wales U20 League | 2024/03/09 06:00 | Manly United U20 v Rockdale Ilinden FC U20 | W | 1-2 |
| Australia New South Wales U20 League | 2024/03/05 08:30 | Rockdale Ilinden FC U20 v St George Saints U20 | W | 2-1 |
| Australia New South Wales U20 League | 2024/03/03 02:00 | Western Sydney Wanderers U20 v Rockdale Ilinden FC U20 | L | 3-1 |
| Australia New South Wales U20 League | 2024/02/25 02:00 | Rockdale Ilinden FC U20 v Marconi Stallions U20 | L | 1-3 |
| 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 |
| Australia New South Wales U20 League | 2024/03/02 08:00 | Sydney Olympic U20 v Sydney United U20 | W | 3-0 |
| Australia New South Wales U20 League | 2024/02/27 08:00 | Sydney Olympic U20 v St George City FA U20 | L | 2-5 |
| Australia New South Wales U20 League | 2024/02/17 03:45 | Sydney Olympic U20 v Hills United FC U20 | L | 2-4 |