| 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 | 2017/03/19 01:45 | Sydney Olympic U20 v Wollongong Wolves U20 | L | 4-0 |
| Australia New South Wales U20 League | 2019/06/09 03:05 | Wollongong Wolves U20 v Sydney United U20 | W | 3-0 |
| Australia New South Wales U20 League | 2019/06/01 06:00 | Wollongong Wolves U20 v Apia L Tigers U20 | L | 1-2 |
| Australia New South Wales U20 League | 2019/05/26 03:03 | Manly United U20 v Wollongong Wolves U20 | W | 1-2 |
| Australia New South Wales U20 League | 2019/05/18 07:05 | Marconi Stallions U20 v Wollongong Wolves U20 | L | 3-2 |
| Australia New South Wales U20 League | 2019/05/11 06:02 | Wollongong Wolves U20 v Rockdale City Suns U20 | L | 0-2 |
| Australia New South Wales U20 League | 2019/05/05 03:04 | Wollongong Wolves U20 v Blacktown City U20 | L | 0-3 |
| Australia New South Wales U20 League | 2019/04/27 06:30 | Sutherland Sharks U20 v Wollongong Wolves U20 | W | 1-2 |
| Australia New South Wales U20 League | 2019/04/21 05:00 | Hakoah Sydney City East U20 v Wollongong Wolves U20 | W | 1-3 |
| Australia New South Wales U20 League | 2019/06/09 03:03 | Blacktown City U20 v Sydney Olympic U20 | D | 1-1 |
| Australia New South Wales U20 League | 2019/06/02 03:47 | Sydney Olympic U20 v Mt Druitt Town Rangers U20 | W | 2-1 |
| Australia New South Wales U20 League | 2019/05/25 06:33 | Sutherland Sharks U20 v Sydney Olympic U20 | L | 1-0 |
| Australia New South Wales U20 League | 2019/05/17 08:00 | Sydney Olympic U20 v Sydney FC U20 | L | 1-2 |
| Australia New South Wales U20 League | 2019/05/12 05:06 | Sydney United U20 v Sydney Olympic U20 | L | 3-0 |
| Australia New South Wales U20 League | 2019/05/04 07:02 | Marconi Stallions U20 v Sydney Olympic U20 | D | 1-1 |
| Australia New South Wales U20 League | 2019/04/25 04:32 | Sydney Olympic U20 v Apia L Tigers U20 | L | 0-2 |
| Australia New South Wales U20 League | 2019/04/19 04:35 | Sydney Olympic U20 v Manly United U20 | W | 3-1 |