| Australia New South Wales U20 League | 2021/04/06 08:45 | Sydney Olympic U20 v Wollongong Wolves U20 | L | 4-1 |
| 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 | W | 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 | L | 1-0 |
| Australia New South Wales U20 League | 2018/08/05 03:00 | Wollongong Wolves U20 v Sydney Olympic U20 | W | 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 | 2021/06/02 09:30 | Wollongong Wolves U20 v Sutherland Sharks U20 | L | 0-3 |
| Australia New South Wales U20 League | 2021/05/29 07:00 | Mt Druitt Town Rangers U20 v Wollongong Wolves U20 | L | 3-0 |
| Australia New South Wales U20 League | 2021/05/22 07:00 | Manly United U20 v Wollongong Wolves U20 | W | 0-2 |
| Australia New South Wales U20 League | 2021/05/16 02:30 | Wollongong Wolves U20 v Rockdale Ilinden FC U20 | D | 2-2 |
| Australia New South Wales U20 League | 2021/05/02 06:30 | Sydney FC U20 v Wollongong Wolves U20 | L | 1-0 |
| Australia New South Wales U20 League | 2021/04/24 07:00 | Apia L Tigers U20 v Wollongong Wolves U20 | D | 4-4 |
| Australia New South Wales U20 League | 2021/04/11 02:30 | Sydney United U20 v Wollongong Wolves U20 | W | 0-4 |
| Australia New South Wales U20 League | 2021/04/06 08:45 | Sydney Olympic U20 v Wollongong Wolves U20 | L | 4-1 |
| 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 | 2021/04/25 03:45 | Sydney Olympic U20 v Bull FC Academy U20 | W | 2-1 |
| Australia New South Wales U20 League | 2021/04/17 06:00 | Marconi Stallions U20 v Sydney Olympic U20 | L | 2-0 |
| Australia New South Wales U20 League | 2021/04/10 07:00 | Manly United U20 v Sydney Olympic U20 | L | 1-0 |