| 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 | 2021/06/20 03:45 | Sydney Olympic U20 v Mt Druitt Town Rangers U20 | W | 1-0 |
| Australia New South Wales U20 League | 2021/06/12 05:15 | Sydney Olympic U20 v Sydney FC U20 | D | 0-0 |
| Australia New South Wales U20 League | 2021/06/06 02:30 | Wollongong Wolves U20 v Sydney Olympic U20 | L | 3-0 |
| Australia New South Wales U20 League | 2021/05/30 01:00 | Apia L Tigers U20 v Sydney Olympic U20 | L | 2-0 |
| 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 | 2021/05/16 02:30 | Sydney United U20 v Sydney Olympic U20 | W | 1-5 |
| Australia New South Wales U20 League | 2021/05/09 03:45 | Sydney Olympic U20 v Blacktown City U20 | D | 1-1 |
| Australia New South Wales U20 League | 2021/05/01 03:30 | Sutherland Sharks U20 v Sydney Olympic U20 | W | 0-4 |
| Australia New South Wales U20 League | 2022/03/06 13:00 | Blacktown City U20 v Rockdale Ilinden FC U20 | D | 2-2 |
| Australia New South Wales U20 League | 2022/03/06 02:00 | Blacktown City U20 v Rockdale Ilinden FC U20 | D | 2-2 |
| Australia Friendlies | 2022/02/12 06:18 | Rockdale Ilinden FC U20 v St George Saints U20 | L | 0-2 |
| Australia New South Wales U20 League | 2021/06/20 03:00 | Apia L Tigers U20 v Rockdale Ilinden FC U20 | W | 0-2 |
| Australia New South Wales U20 League | 2021/06/13 03:00 | Rockdale Ilinden FC U20 v Blacktown City U20 | W | 2-1 |
| Australia New South Wales U20 League | 2021/06/05 07:00 | Manly United U20 v Rockdale Ilinden FC U20 | W | 1-2 |
| Australia New South Wales U20 League | 2021/05/30 03:00 | Rockdale Ilinden FC U20 v Marconi Stallions U20 | L | 1-7 |
| Australia New South Wales U20 League | 2021/05/23 02:45 | Sydney Olympic U20 v Rockdale Ilinden FC U20 | D | 0-0 |