

Team 2019 Scheduals| 10 Mar |
r01 ![]() ![]() | Los Angeles FCLos Angeles F | 4 - 1 | Portland TimbersPortland Timb |
| 17 Mar |
r01 ![]() ![]() | FC CincinnatiFC Cincinnati | 3 - 0 | Portland TimbersPortland Timb |
| 01 Apr |
r01 ![]() ![]() | L.A. GalaxyL.A. Galaxy | 2 - 1 | Portland TimbersPortland Timb |
| 07 Apr |
r01 ![]() ![]() | San Jose EarthquakesSan Jose Eart | 3 - 0 | Portland TimbersPortland Timb |
| 14 Apr |
r01 ![]() | FC DallasFC Dallas | 2 - 1 | Portland TimbersPortland Timb |
| 21 Apr |
r01 ![]() | Columbus CrewColumbus Crew | 1 - 3 | Portland TimbersPortland Timb |
| 27 Apr |
r01 ![]() ![]() | Toronto FCToronto FC | 1 - 2 | Portland TimbersPortland Timb |
| 05 May |
r01 ![]() | Real Salt LakeReal Salt Lak | 1 - 2 | Portland TimbersPortland Timb |
| 11 May |
r01 ![]() | Vancouver WhitecapsVancouver Whi | 1 - 0 | Portland TimbersPortland Timb |
| 16 May |
r01 | Houston DynamoHouston Dynam | 1 - 1 | Portland TimbersPortland Timb |
| 26 May |
r01 ![]() ![]() | Philadelphia UnionPhiladelphia | 1 - 3 | Portland TimbersPortland Timb |
| 02 Jun |
r01 ![]() ![]() | Portland TimbersPortland Timb | 2 - 3 | Los Angeles FCLos Angeles F |
| 23 Jun |
r01 | Portland TimbersPortland Timb | 4 - 0 | Houston DynamoHouston Dynam |
| 27 Jun |
r01 | Montreal ImpactMontreal Impa | 2 - 1 | Portland TimbersPortland Timb |
| 01 Jul |
r01 ![]() ![]() | Portland TimbersPortland Timb | 1 - 0 | FC DallasFC Dallas |
| 07 Jul |
r01 ![]() ![]() | New York CityNew York City | 0 - 1 | Portland TimbersPortland Timb |
| 14 Jul |
r01 ![]() ![]() | Portland TimbersPortland Timb | 2 - 2 | Colorado RapidsColorado Rapi |
| 19 Jul |
r01 ![]() | Portland TimbersPortland Timb | 1 - 1 | Orlando CityOrlando City |
| 22 Jul |
r01 | Seattle Sounders FCSeattle Sound | 1 - 2 | Portland TimbersPortland Timb |
| 28 Jul |
r01 ![]() ![]() | Portland TimbersPortland Timb | 4 - 0 | L.A. GalaxyL.A. Galaxy |
| 04 Aug |
r01 ![]() | Minnesota UnitedMinnesota Uni | 1 - 0 | Portland TimbersPortland Timb |
| 11 Aug |
r01 | Portland TimbersPortland Timb | 3 - 1 | Vancouver WhitecapsVancouver Whi |
| 15 Aug |
r01 ![]() ![]() | Portland TimbersPortland Timb | 3 - 2 | Chicago FireChicago Fire |
| 19 Aug |
r01 ![]() ![]() | Portland TimbersPortland Timb | 0 - 2 | Atlanta UnitedAtlanta Unite |
| 24 Aug |
r01 ![]() ![]() | Portland TimbersPortland Timb | 1 - 2 | Seattle Sounders FCSeattle Sound |
| 01 Sep |
r01 ![]() ![]() | Portland TimbersPortland Timb | 1 - 0 | Real Salt LakeReal Salt Lak |
| 08 Sep |
r01 ![]() ![]() | Portland TimbersPortland Timb | 2 - 1 | Sporting Kansas CitySporting Kans |
| 15 Sep |
r01 ![]() ![]() | Portland TimbersPortland Timb | 0 - 1 | DC UnitedDC United |
| 19 Sep |
r01 ![]() ![]() | Portland TimbersPortland Timb | 0 - 2 | New York Red BullsNew York Red |
| 22 Sep |
r01 | Portland TimbersPortland Timb | 0 - 0 | Minnesota UnitedMinnesota Uni |
| 26 Sep |
r01 ![]() | Portland TimbersPortland Timb | 2 - 2 | New England Rev.New England R |
| 30 Sep |
r01 ![]() | Sporting Kansas CitySporting Kans | 2 - 2 | Portland TimbersPortland Timb |
| 06 Oct |
r01 ![]() | Portland TimbersPortland Timb | 3 - 1 | San Jose EarthquakesSan Jose Eart |