| Australia New South Wales U20 League | 2024/04/14 02:30 | Rockdale Ilinden FC U20 v Sydney Olympic U20 | L | 3-2 |
| 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 | L | 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 | 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 | 2024/07/12 09:00 | Sydney Olympic U20 v Central Coast Mariners U20 | L | 0-5 |
| Australia New South Wales U20 League | 2024/07/07 03:00 | Wollongong Wolves U20 v Sydney Olympic U20 | W | 0-3 |
| Australia New South Wales U20 League | 2024/06/21 09:00 | Sydney Olympic U20 v Apia L Tigers U20 | L | 0-2 |
| Australia New South Wales U20 League | 2024/06/11 09:30 | Marconi Stallions U20 v Sydney Olympic U20 | L | 3-0 |
| Australia New South Wales U20 League | 2024/06/09 03:00 | Sydney United U20 v Sydney Olympic U20 | D | 1-1 |
| Australia New South Wales U20 League | 2024/06/01 07:00 | St George City FA U20 v Sydney Olympic U20 | L | 3-2 |
| Australia New South Wales U20 League | 2024/05/25 07:00 | Hills United FC U20 v Sydney Olympic U20 | D | 0-0 |
| Australia New South Wales U20 League | 2024/05/17 07:30 | Sydney FC U20 v Sydney Olympic U20 | L | 4-1 |
| Australia New South Wales U20 League | 2024/07/14 03:00 | Rockdale Ilinden FC U20 v Sydney United U20 | W | 2-0 |
| Australia New South Wales U20 League | 2024/07/06 09:44 | NWS Spirit FC U20 v Rockdale Ilinden FC U20 | W | 2-5 |
| Australia New South Wales U20 League | 2024/06/30 03:00 | Rockdale Ilinden FC U20 v Hills United FC U20 | W | 4-2 |
| Australia New South Wales U20 League | 2024/06/23 03:00 | Blacktown City U20 v Rockdale Ilinden FC U20 | L | 3-1 |
| Australia New South Wales U20 League | 2024/06/16 03:00 | Rockdale Ilinden FC U20 v Manly United U20 | W | 1-0 |
| Australia New South Wales U20 League | 2024/06/12 08:00 | St George Saints U20 v Rockdale Ilinden FC U20 | W | 1-4 |
| Australia New South Wales U20 League | 2024/06/09 03:00 | Rockdale Ilinden FC U20 v Western Sydney Wanderers U20 | W | 2-0 |
| Australia New South Wales U20 League | 2024/05/26 03:00 | Rockdale Ilinden FC U20 v St George City FA U20 | W | 3-2 |