| Australia New South Wales U20 League | 2023/08/25 09:00 | Sydney Olympic U20 v Sydney United U20 | L | 0-4 |
| Australia New South Wales U20 League | 2023/08/19 06:45 | Marconi Stallions U20 v Sydney Olympic U20 | D | 1-1 |
| Australia New South Wales U20 League | 2023/08/13 10:03 | Wollongong Wolves U20 v Sydney Olympic U20 | W | 0-1 |
| Australia New South Wales U20 League | 2023/08/09 09:00 | Sydney Olympic U20 v Central Coast Mariners U20 | L | 1-3 |
| Australia New South Wales U20 League | 2023/08/05 04:00 | Sydney Olympic U20 v Apia L Tigers U20 | W | 1-0 |
| Australia New South Wales U20 League | 2023/07/22 04:00 | Sydney Olympic U20 v Mt Druitt Town Rangers U20 | L | 2-3 |
| Australia New South Wales U20 League | 2023/07/08 09:52 | NWS Spirit FC U20 v Sydney Olympic U20 | D | 2-2 |
| Australia New South Wales U20 League | 2023/07/01 04:00 | Sydney Olympic U20 v Blacktown City U20 | L | 0-2 |
| Australia NSW League 1 U20 | 2023/08/26 07:00 | Hills United FC U20 v Bonnyrigg White Eagles U20 | L | 1-3 |
| Australia NSW League 1 U20 | 2023/08/23 09:15 | Hills United FC U20 v Canterbury Bankstown FC U20 | W | 5-1 |
| Australia NSW League 1 U20 | 2023/08/19 05:00 | Hakoah Sydney City East U20 v Hills United FC U20 | W | 2-3 |
| Australia NSW League 1 U20 | 2023/08/05 07:00 | St George Saints U20 v Hills United FC U20 | L | 4-1 |
| Australia NSW League 1 U20 | 2023/07/29 07:10 | Hills United FC U20 v Blacktown Spartans U20 | W | 3-2 |
| Australia NSW League 1 U20 | 2023/07/22 07:00 | Dulwich Hill U20 v Hills United FC U20 | W | 1-2 |
| Australia NSW League 1 U20 | 2023/07/15 07:00 | Hills United FC U20 v Mounties Wanderers U20 | D | 2-2 |
| Australia NSW League 1 U20 | 2023/07/08 07:00 | Macarthur Rams U20 v Hills United FC U20 | D | 0-0 |