| U20 Victoria Premier League 2 | 2018/06/08 08:15 | Bentleigh Greens v Oakleigh Cannons | W | 2-1 |
| U20 Victoria Premier League 2 | 2018/03/02 07:20 | Oakleigh Cannons v Bentleigh Greens | D | 2-2 |
| U20 Victoria Premier League 2 | 2017/08/20 03:00 | Bentleigh Greens v Oakleigh Cannons | W | 8-0 |
| U20 Victoria Premier League 2 | 2017/05/12 08:15 | Oakleigh Cannons v Bentleigh Greens | L | 3-0 |
| U20 Victoria Premier League 2 | 2019/03/23 06:00 | Dandenong Thunder v Bentleigh Greens | W | 0-5 |
| U20 Victoria Premier League 2 | 2019/03/15 07:14 | Bentleigh Greens v Hume City | D | 1-1 |
| U20 Victoria Premier League 2 | 2019/03/10 03:59 | Melbourne Knights v Bentleigh Greens | L | 5-1 |
| U20 Victoria Premier League 2 | 2019/03/01 07:19 | Bentleigh Greens v Green Gully Cavaliers | W | 2-1 |
| U20 Victoria Premier League 2 | 2019/02/23 00:04 | Pascoe Vale v Bentleigh Greens | D | 1-1 |
| U20 Victoria Premier League 2 | 2019/02/15 07:19 | Bentleigh Greens v South Melbourne | L | 1-2 |
| U20 Victoria Premier League 2 | 2018/09/02 03:00 | Bentleigh Greens v Bulleen Lions | W | 4-3 |
| U20 Victoria Premier League 2 | 2018/08/11 02:32 | Avondale v Bentleigh Greens | L | 5-2 |
| U20 Victoria Premier League 2 | 2019/03/22 07:15 | Oakleigh Cannons v Heidelberg Uts. | D | 1-1 |
| U20 Victoria Premier League 2 | 2019/03/16 05:05 | Altona Magic v Oakleigh Cannons | D | 1-1 |
| U20 Victoria Premier League 2 | 2019/03/11 07:15 | Kingston City v Oakleigh Cannons | L | 3-0 |
| U20 Victoria Premier League 2 | 2019/03/01 07:15 | Oakleigh Cannons v Dandenong Thunder | L | 0-2 |
| U20 Victoria Premier League 2 | 2019/02/24 04:04 | Hume City v Oakleigh Cannons | D | 3-3 |
| U20 Victoria Premier League 2 | 2019/02/15 07:21 | Oakleigh Cannons v Melbourne Knights | W | 2-1 |
| U20 Victoria Premier League 2 | 2018/09/02 03:03 | Northcote City v Oakleigh Cannons | W | 1-4 |
| U20 Victoria Premier League 2 | 2018/08/24 08:15 | Oakleigh Cannons v Pascoe Vale | L | 2-5 |