Head to Head
| Australia South Australia Premier League | 2020/08/08 08:30 | Adelaide Olympic v Cumberland United | D | 0-0 |
| Australia FFA Cup | 2019/05/04 07:33 | Cumberland United v Adelaide Olympic | L | 2-3 |
| Australia FFA Cup | 2018/05/05 05:01 | Cumberland United v Adelaide Olympic | W | 2-1 |
| Australia South Australia Premier League | 2017/07/08 09:30 | Cumberland United v Adelaide Olympic | L | 1-2 |
| Australia South Australia Premier League | 2017/04/01 08:30 | Adelaide Olympic v Cumberland United | L | 3-2 |
Home History
| Australia South Australia Premier League | 2020/09/19 05:30 | Modbury Jets v Cumberland United | W | 1-2 |
| Australia South Australia Premier League | 2020/09/12 07:30 | Cumberland United v Croydon FC | L | 1-4 |
| Australia South Australia Premier League | 2020/09/04 10:45 | Adelaide Croatia Raiders v Cumberland United | W | 0-1 |
| Australia South Australia Premier League | 2020/08/29 07:30 | Cumberland United v Campbelltown City | L | 0-1 |
| Australia South Australia Premier League | 2020/08/22 05:30 | Adelaide United NPL v Cumberland United | W | 0-3 |
| Australia South Australia Premier League | 2020/08/15 05:30 | Cumberland United v Adelaide Blue Eagles | D | 2-2 |
| Australia South Australia Premier League | 2020/08/08 08:30 | Adelaide Olympic v Cumberland United | D | 0-0 |
| Australia South Australia Premier League | 2020/08/01 05:30 | Cumberland United v Adelaide Croatia Raiders | D | 1-1 |
Away History
| Australia South Australia Premier League | 2020/09/19 09:30 | Adelaide Olympic v Adelaide Blue Eagles | W | 1-0 |
| Australia South Australia Premier League | 2020/09/12 08:30 | Adelaide Olympic v Modbury Jets | L | 2-4 |
| Australia South Australia Premier League | 2020/09/05 05:00 | Croydon FC v Adelaide Olympic | L | 1-0 |
| Australia South Australia Premier League | 2020/08/29 08:30 | Adelaide Olympic v Adelaide Croatia Raiders | D | 4-4 |
| Australia South Australia Premier League | 2020/08/21 10:00 | Campbelltown City v Adelaide Olympic | W | 1-2 |
| Australia South Australia Premier League | 2020/08/15 05:30 | Adelaide City v Adelaide Olympic | L | 1-0 |
| Australia South Australia Premier League | 2020/08/08 08:30 | Adelaide Olympic v Cumberland United | D | 0-0 |
| Australia South Australia Premier League | 2020/08/01 08:30 | Adelaide Olympic v Croydon FC | L | 2-4 |