| Ausztrál New South Wales League - U20 | 2023/06/11 03:00 | Rockdale Ilinden FC - U20 v Sydney Olympic - U20 | D | 2-2 |
| Ausztrál New South Wales League - U20 | 2023/02/26 01:45 | Sydney Olympic - U20 v Rockdale Ilinden FC - U20 | W | 2-5 |
| Ausztrál New South Wales League - U20 | 2022/05/29 04:00 | Rockdale Ilinden FC - U20 v Sydney Olympic - U20 | D | 1-1 |
| Ausztrál New South Wales League - U20 | 2022/03/13 02:45 | Sydney Olympic - U20 v Rockdale Ilinden FC - U20 | L | 2-1 |
| Ausztrál New South Wales League - U20 | 2021/05/23 02:45 | Sydney Olympic - U20 v Rockdale Ilinden FC - U20 | D | 0-0 |
| Ausztrál New South Wales League - U20 | 2021/03/07 02:00 | Rockdale Ilinden FC - U20 v Sydney Olympic - U20 | L | 0-3 |
| Ausztrál New South Wales League - U20 | 2024/04/07 03:00 | Sydney United - U20 v Rockdale Ilinden FC - U20 | D | 2-2 |
| Ausztrál New South Wales League - U20 | 2024/03/31 02:00 | Rockdale Ilinden FC - U20 v NWS Spirit FC - U20 | W | 5-3 |
| Ausztrál New South Wales League - U20 | 2024/03/23 06:00 | Hills United FC - U20 v Rockdale Ilinden FC - U20 | W | 2-3 |
| Ausztrál New South Wales League - U20 | 2024/03/17 02:00 | Rockdale Ilinden FC - U20 v Blacktown City - U20 | W | 1-0 |
| Ausztrál New South Wales League - U20 | 2024/03/09 06:00 | Manly United - U20 v Rockdale Ilinden FC - U20 | W | 1-2 |
| Ausztrál New South Wales League - U20 | 2024/03/05 08:30 | Rockdale Ilinden FC - U20 v St George Saints - U20 | W | 2-1 |
| Ausztrál New South Wales League - U20 | 2024/03/03 02:00 | Western Sydney Wanderers U20 v Rockdale Ilinden FC - U20 | L | 3-1 |
| Ausztrál New South Wales League - U20 | 2024/02/25 02:00 | Rockdale Ilinden FC - U20 v Marconi Stallions - U20 | L | 1-3 |
| Ausztrál New South Wales League - U20 | 2024/03/30 08:00 | Sydney Olympic - U20 v Wollongong Wolves - U20 | W | 5-2 |
| Ausztrál New South Wales League - U20 | 2024/03/22 06:30 | Manly United - U20 v Sydney Olympic - U20 | L | 2-0 |
| Ausztrál New South Wales League - U20 | 2024/03/16 09:00 | Apia L Tigers - U20 v Sydney Olympic - U20 | L | 1-0 |
| Ausztrál New South Wales League - U20 | 2024/03/09 07:40 | Sutherland Sharks - U20 v Sydney Olympic - U20 | L | 3-0 |
| Ausztrál New South Wales League - U20 | 2024/03/05 08:00 | Sydney Olympic - U20 v Marconi Stallions - U20 | W | 1-0 |
| Ausztrál New South Wales League - U20 | 2024/03/02 08:00 | Sydney Olympic - U20 v Sydney United - U20 | W | 3-0 |
| Ausztrál New South Wales League - U20 | 2024/02/27 08:00 | Sydney Olympic - U20 v St George City FA - U20 | L | 2-5 |
| Ausztrál New South Wales League - U20 | 2024/02/17 03:45 | Sydney Olympic - U20 v Hills United FC - U20 | L | 2-4 |