Stadium: Providence Park Round: 199
Referee: Armando Villarreal Home Manager: Giovanni Savarese Away Manager: Ronny Deila
| USA MLS is Back Tournament | 2020/08/02 02:30 | New York City FC v Portland Timbers | W | 1-3 |
| USA MLS | 2019/07/07 22:30 | New York City FC v Portland Timbers | W | 0-1 |
| USA MLS | 2018/04/22 22:00 | Portland Timbers v New York City FC | W | 3-0 |
| USA MLS | 2017/09/09 21:30 | New York City FC v Portland Timbers | W | 0-1 |
| USA MLS | 2016/05/15 23:30 | Portland Timbers v New York City FC | L | 1-2 |
| USA MLS | 2015/04/19 23:00 | New York City FC v Portland Timbers | W | 0-1 |
| USA MLS | 2021/10/03 21:30 | Portland Timbers v Inter Miami CF | W | 1-0 |
| USA MLS | 2021/09/30 02:30 | Los Angeles FC v Portland Timbers | W | 1-2 |
| USA MLS | 2021/09/26 02:30 | Portland Timbers v Real Salt Lake | W | 6-1 |
| USA MLS | 2021/09/19 23:30 | Portland Timbers v Los Angeles FC | W | 2-1 |
| USA MLS | 2021/09/16 02:00 | Portland Timbers v Colorado Rapids | D | 2-2 |
| USA MLS | 2021/09/11 02:00 | Vancouver Whitecaps v Portland Timbers | W | 0-1 |
| USA MLS | 2021/09/04 00:00 | Houston Dynamo v Portland Timbers | W | 0-2 |
| USA MLS | 2021/08/30 02:30 | Seattle Sounders v Portland Timbers | W | 0-2 |
| USA MLS | 2021/10/03 16:00 | New York City FC v Nashville SC | D | 0-0 |
| USA MLS | 2021/09/30 00:00 | Chicago Fire v New York City FC | L | 2-0 |
| USA MLS | 2021/09/26 00:00 | New York City FC v New York Red Bulls | L | 0-1 |
| USA MLS | 2021/09/23 00:00 | New York Red Bulls v New York City FC | D | 1-1 |
| USA MLS | 2021/09/18 23:30 | FC Cincinnati v New York City FC | W | 1-2 |
| USA MLS | 2021/09/14 23:30 | New York City FC v FC Dallas | D | 3-3 |
| USA MLS | 2021/09/11 23:00 | New England Revolution v New York City FC | L | 2-1 |
| USA MLS | 2021/09/03 23:30 | Nashville SC v New York City FC | L | 3-1 |