| | | |
| March 7, 2020 | L | Portland Timbers 2 1 at Phoenix Rising FC 6 | Final |
| March 14, 2020 | | Portland Timbers 2 at El Paso Locomotive FC | Ppd. |
| March 22, 2020 | | Colorado Springs Switchbacks FC at Portland Timbers 2 | Ppd. |
| March 28, 2020 | | Portland Timbers 2 at Reno 1868 FC | Ppd. |
| April 5, 2020 | | San Antonio FC at Portland Timbers 2 | Ppd. |
| April 12, 2020 | | Real Monarchs at Portland Timbers 2 | Ppd. |
| April 18, 2020 | | Portland Timbers 2 at OKC Energy FC | Ppd. |
| April 26, 2020 | | San Diego Loyal at Portland Timbers 2 | Ppd. |
| May 2, 2020 | | Portland Timbers 2 at FC Tulsa | Ppd. |
| May 10, 2020 | | Sacramento Republic FC at Portland Timbers 2 | Ppd. |
| May 16, 2020 | | Tacoma Defiance at Portland Timbers 2 | Ppd. |
| May 23, 2020 | | Portland Timbers 2 at Austin Bold FC | Ppd. |
| May 27, 2020 | | New Mexico United at Portland Timbers 2 | Ppd. |
| June 9, 2020 | | Las Vegas Lights FC at Portland Timbers 2 | Ppd. |
| June 13, 2020 | | Portland Timbers 2 at Orange County SC | Ppd. |
| June 21, 2020 | | Portland Timbers 2 at LA Galaxy II | Ppd. |
| July 3, 2020 | | Portland Timbers 2 at San Diego Loyal | Ppd. |
| July 18, 2020 | L | Portland Timbers 2 0 at Tacoma Defiance 3 | Final |
| July 29, 2020 | L | Reno 1868 FC 4 at Portland Timbers 2 1 | Final |
| August 3, 2020 | L | Tacoma Defiance 4 at Portland Timbers 2 0 | Final |
| August 8, 2020 | L | Sacramento Republic FC 1 at Portland Timbers 2 0 | Final |
| August 15, 2020 | L | Portland Timbers 2 2 at Reno 1868 FC 5 | Final (7) |
| August 22, 2020 | L | Portland Timbers 2 1 at Sacramento Republic FC 2 | Final |
| August 26, 2020 | L | LA Galaxy II 3 at Portland Timbers 2 2 | Final (7) |
| August 30, 2020 | | Tacoma Defiance at Portland Timbers 2 | Ppd. |
| September 2, 2020 | L | Sacramento Republic FC 2 at Portland Timbers 2 1 | Final |
| September 5, 2020 | L | Portland Timbers 2 1 at Reno 1868 FC 7 | Final |
| September 16, 2020 | W | Portland Timbers 2 2 at Real Monarchs 1 | Final |
| September 20, 2020 | L | Reno 1868 FC 5 at Portland Timbers 2 2 | Final |
| September 24, 2020 | W | Tacoma Defiance 1 at Portland Timbers 2 3 | Final |
| September 27, 2020 | L | Portland Timbers 2 1 at Tacoma Defiance 2 | Final |
| October 3, 2020 | L | Portland Timbers 2 0 at Sacramento Republic FC 4 | Final |
Portland Timbers 2 Schedule
