[10] Portland Timbers 1-1 Orlando City SC [9] 2019-07-19 02:00
Stadium: Providence Park Round: 1
Referee: Joseph Dickerson Home Manager: Giovanni Savarese Away Manager: James O'Connor
Head to Head
| 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 |