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Previous matches:
| Portland Timbers | 1 | 2 | Chicago |
| MLS - 22.06.2023 | |||
| Portland Timbers | 3 | 2 | Chicago |
| MLS - 15.08.2019 | |||
| Chicago | 2 | 2 | Portland Timbers |
| MLS - 31.03.2018 | |||
| Portland Timbers | 2 | 2 | Chicago |
| MLS - 06.07.2017 | |||
| Chicago | 1 | 1 | Portland Timbers |
| MLS - 29.05.2016 | |||
| Portland Timbers | 1 | 0 | Chicago |
| MLS - 08.08.2015 | |||
| Portland Timbers | 1 | 1 | Chicago |
| MLS - 16.03.2014 | |||
| Chicago | 2 | 2 | Portland Timbers |
| MLS - 09.06.2013 | |||
| Portland Timbers | 2 | 1 | Chicago |
| MLS - 20.05.2012 | |||