| 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 Friendlies | 2020/02/15 03:22 | Sutherland Sharks U20 v Sydney Olympic U20 | D | 1-1 |
| Australia Friendlies | 2020/02/01 06:03 | Manly United U20 v Sydney Olympic U20 | D | 0-0 |
| Australia New South Wales U20 League | 2019/08/04 02:45 | Sydney Olympic U20 v Sydney United U20 | W | 3-0 |
| Australia New South Wales U20 League | 2019/07/28 03:48 | Sydney Olympic U20 v Marconi Stallions U20 | W | 2-0 |
| Australia New South Wales U20 League | 2019/07/21 03:17 | Apia L Tigers U20 v Sydney Olympic U20 | L | 2-0 |
| Australia New South Wales U20 League | 2019/07/07 03:02 | Manly United U20 v Sydney Olympic U20 | W | 0-1 |
| Australia New South Wales U20 League | 2019/06/30 03:45 | Sydney Olympic U20 v Rockdale City Suns U20 | L | 0-1 |
| Australia New South Wales U20 League | 2019/06/26 10:02 | Sydney Olympic U20 v Hakoah Sydney City East U20 | W | 2-1 |
| Australia New South Wales U20 League | 2019/08/11 03:03 | Wollongong Wolves U20 v Marconi Stallions U20 | L | 1-2 |
| Australia New South Wales U20 League | 2019/08/04 04:31 | Rockdale City Suns U20 v Wollongong Wolves U20 | L | 1-0 |
| Australia New South Wales U20 League | 2019/07/28 03:04 | Blacktown City U20 v Wollongong Wolves U20 | L | 1-0 |
| Australia New South Wales U20 League | 2019/07/20 06:02 | Wollongong Wolves U20 v Sutherland Sharks U20 | L | 0-2 |
| Australia New South Wales U20 League | 2019/07/07 03:03 | Wollongong Wolves U20 v Hakoah Sydney City East U20 | W | 3-1 |
| Australia New South Wales U20 League | 2019/06/29 07:04 | Mt Druitt Town Rangers U20 v Wollongong Wolves U20 | L | 2-0 |
| 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 | 2019/06/09 03:05 | Wollongong Wolves U20 v Sydney United U20 | W | 3-0 |