| Austraalia New South Wales U20 League | 2023/04/29 06:30 | Sydney Olympic U20 v Wollongong Wolves U20 | W | 1-4 |
| Austraalia New South Wales U20 League | 2022/06/13 03:45 | Sydney Olympic U20 v Wollongong Wolves U20 | D | 1-1 |
| Austraalia New South Wales U20 League | 2022/04/27 07:30 | Wollongong Wolves U20 v Sydney Olympic U20 | L | 1-2 |
| Austraalia New South Wales U20 League | 2021/06/06 02:30 | Wollongong Wolves U20 v Sydney Olympic U20 | W | 3-0 |
| Austraalia New South Wales U20 League | 2021/04/06 08:45 | Sydney Olympic U20 v Wollongong Wolves U20 | L | 4-1 |
| Austraalia New South Wales U20 League | 2020/09/20 02:30 | Wollongong Wolves U20 v Sydney Olympic U20 | D | 1-1 |
| Austraalia New South Wales U20 League | 2020/03/01 02:51 | Sydney Olympic U20 v Wollongong Wolves U20 | W | 0-3 |
| Austraalia New South Wales U20 League | 2019/06/23 03:03 | Wollongong Wolves U20 v Sydney Olympic U20 | D | 1-1 |
| Austraalia New South Wales U20 League | 2023/08/06 03:00 | Wollongong Wolves U20 v Manly United U20 | D | 0-0 |
| Austraalia New South Wales U20 League | 2023/08/02 09:30 | Wollongong Wolves U20 v NWS Spirit FC U20 | W | 3-2 |
| Austraalia New South Wales U20 League | 2023/07/30 03:00 | Sydney United U20 v Wollongong Wolves U20 | L | 7-0 |
| Austraalia New South Wales U20 League | 2023/06/30 07:30 | Wollongong Wolves U20 v St George City FA U20 | L | 0-1 |
| Austraalia New South Wales U20 League | 2023/06/25 03:00 | Rockdale Ilinden FC U20 v Wollongong Wolves U20 | L | 4-3 |
| Austraalia New South Wales U20 League | 2023/06/03 09:15 | Marconi Stallions U20 v Wollongong Wolves U20 | L | 2-0 |
| Austraalia New South Wales U20 League | 2023/05/26 07:30 | Wollongong Wolves U20 v Sutherland Sharks U20 | D | 1-1 |
| Austraalia New South Wales U20 League | 2023/05/20 09:57 | APIA L Tigers U20 v Wollongong Wolves U20 | L | 5-2 |
| Austraalia New South Wales U20 League | 2023/08/09 09:00 | Sydney Olympic U20 v Central Coast Mariners U20 | L | 1-3 |
| Austraalia New South Wales U20 League | 2023/08/05 04:00 | Sydney Olympic U20 v APIA L Tigers U20 | W | 1-0 |
| Austraalia New South Wales U20 League | 2023/07/22 04:00 | Sydney Olympic U20 v Mt Druitt Town Rangers U20 | L | 2-3 |
| Austraalia New South Wales U20 League | 2023/07/08 09:52 | NWS Spirit FC U20 v Sydney Olympic U20 | D | 2-2 |
| Austraalia New South Wales U20 League | 2023/07/01 04:00 | Sydney Olympic U20 v Blacktown City U20 | L | 0-2 |
| Austraalia New South Wales U20 League | 2023/06/18 07:30 | Sydney Olympic U20 v St George City FA U20 | W | 1-0 |
| Austraalia New South Wales U20 League | 2023/06/11 03:00 | Rockdale Ilinden FC U20 v Sydney Olympic U20 | D | 2-2 |
| Austraalia New South Wales U20 League | 2023/05/27 06:30 | Sydney Olympic U20 v Manly United U20 | L | 0-3 |