Portland Timbers 2-1 Orlando City SC 2020-08-12 00:30
Stadium: ESPN Wide World of Sports Complex Round: 1
Referee: Ismail Elfath Home Manager: Giovanni Savarese Away Manager: Oscar Pareja
Head to Head
| USA MLS | 2019/07/19 02:00 | Portland Timbers v Orlando City SC | D | 1-1 |
| USA MLS | 2018/04/08 20:00 | Orlando City SC v Portland Timbers | L | 3-2 |
| USA MLS | 2017/09/25 00:00 | Portland Timbers v Orlando City SC | W | 3-0 |
| USA MLS | 2016/04/04 00:00 | Orlando City SC v Portland Timbers | L | 4-1 |
| USA MLS | 2015/04/12 21:00 | Portland Timbers v Orlando City SC | L | 0-2 |
| USA US Open Cup | 2014/06/18 02:30 | Portland Timbers v Orlando City SC | W | 3-0 |