| 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 | 2019/03/31 03:00 | Hakoah Sydney City East U20 v Sydney Olympic U20 | W | 2-3 |
| Australia New South Wales U20 League | 2019/03/24 02:49 | Sydney Olympic U20 v Blacktown City U20 | W | 3-1 |
| Australia New South Wales U20 League | 2019/03/10 02:48 | Sydney Olympic U20 v Sutherland Sharks U20 | W | 2-1 |
| Australia New South Wales U20 League | 2018/08/12 02:04 | Sydney Olympic U20 v Sydney United U20 | L | 0-4 |
| 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 | 2018/07/29 02:35 | Sydney Olympic U20 v Sutherland Sharks U20 | L | 0-1 |
| Australia New South Wales U20 League | 2018/07/08 05:00 | Rockdale City Suns U20 v Sydney Olympic U20 | W | 1-2 |
| Australia New South Wales U20 League | 2018/07/01 03:06 | Blacktown City U20 v Sydney Olympic U20 | L | 3-1 |
| Australia New South Wales U20 League | 2019/04/03 08:33 | Apia L Tigers U20 v Wollongong Wolves U20 | L | 4-0 |
| Australia New South Wales U20 League | 2019/03/24 04:04 | Sydney United U20 v Wollongong Wolves U20 | W | 1-2 |
| Australia New South Wales U20 League | 2019/03/10 02:02 | Wollongong Wolves U20 v Manly United U20 | W | 2-0 |
| Australia Friendlies | 2019/02/24 05:00 | Rockdale City Suns U20 v Wollongong Wolves U20 | W | 2-3 |
| Australia New South Wales U20 League | 2018/08/18 05:36 | Sydney United U20 v Wollongong Wolves U20 | L | 3-0 |
| Australia New South Wales U20 League | 2018/08/12 03:02 | Marconi Stallions U20 v Wollongong Wolves U20 | L | 2-1 |
| 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 | 2018/07/28 06:59 | Manly United U20 v Wollongong Wolves U20 | W | 1-2 |