| Australia New South Wales U20 League | 2020/09/20 02:30 | Wollongong Wolves U20 v Sydney Olympic U20 | D | 1-1 |
| Australia New South Wales U20 League | 2020/03/01 02:51 | Sydney Olympic U20 v Wollongong Wolves U20 | L | 0-3 |
| Australia New South Wales U20 League | 2019/06/23 03:03 | Wollongong Wolves U20 v Sydney Olympic U20 | D | 1-1 |
| Australia New South Wales U20 League | 2019/04/07 03:56 | Sydney Olympic U20 v Wollongong Wolves U20 | W | 1-0 |
| Australia New South Wales U20 League | 2018/08/05 03:00 | Wollongong Wolves U20 v Sydney Olympic U20 | L | 1-0 |
| Australia New South Wales U20 League | 2018/05/13 02:45 | Sydney Olympic U20 v Wollongong Wolves U20 | D | 1-1 |
| Australia New South Wales U20 League | 2017/06/04 03:03 | Wollongong Wolves U20 v Sydney Olympic U20 | D | 2-2 |
| Australia New South Wales U20 League | 2017/03/19 01:45 | Sydney Olympic U20 v Wollongong Wolves U20 | W | 4-0 |
| Australia New South Wales U20 League | 2021/04/03 06:00 | Mt Druitt Town Rangers U20 v Sydney Olympic U20 | W | 3-4 |
| Australia New South Wales U20 League | 2021/03/28 05:30 | Sydney FC U20 v Sydney Olympic U20 | L | 1-0 |
| Australia New South Wales U20 League | 2021/03/13 02:45 | Sydney Olympic U20 v Apia L Tigers U20 | W | 2-1 |
| 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 | 2021/02/27 02:45 | Sydney Olympic U20 v Sydney United U20 | W | 3-0 |
| Australia Friendlies | 2021/02/06 06:00 | Blacktown City U20 v Sydney Olympic U20 | W | 0-3 |
| Australia New South Wales U20 League | 2020/10/10 06:00 | Mt Druitt Town Rangers U20 v Sydney Olympic U20 | W | 4-5 |
| Australia New South Wales U20 League | 2020/10/03 07:00 | Sydney Olympic U20 v Western Sydney Wanderers U20 | L | 0-3 |
| Australia New South Wales U20 League | 2021/04/02 03:00 | Marconi Stallions U20 v Wollongong Wolves U20 | W | 1-2 |
| Australia New South Wales U20 League | 2021/03/27 23:00 | Wollongong Wolves U20 v Bull FC Academy U20 | W | 1-0 |
| Australia New South Wales U20 League | 2021/03/14 01:30 | Wollongong Wolves U20 v Mt Druitt Town Rangers U20 | L | 0-1 |
| Australia New South Wales U20 League | 2021/03/06 23:00 | Wollongong Wolves U20 v Manly United U20 | L | 0-2 |
| Australia New South Wales U20 League | 2021/02/28 02:00 | Rockdale City Suns U20 v Wollongong Wolves U20 | W | 2-3 |
| Australia New South Wales U20 League | 2021/02/28 02:00 | Rockdale Ilinden FC U20 v Wollongong Wolves U20 | W | 2-3 |
| Australia Friendlies | 2021/01/30 06:00 | Rockdale City Suns U20 v Wollongong Wolves U20 | L | 2-1 |
| Australia New South Wales U20 League | 2020/10/11 01:30 | Wollongong Wolves U20 v Manly United U20 | D | 1-1 |