Timber's eSports player Edgar Guerrero (X_Thiago_Silva_0) finished 7th in the preliminary round, giving him a spot in the Western Quarter Finals.
Guerrero would fall to Sporting Kansas City eSports player Alex Betancourt (SKC Alekzandur) in the Western Quarter Finals to a score of 3–2.
In the 59th minute, Bill Tuiloma was able to head the ball into the net with from a free kick from Diego Valeri that would put the Timbers up 2–0.
The Timbers Army sang the national anthem for the home opener, as is tradition in the MLS era, followed by unveiling their Singin' in the Rain themed tifo.
Adi was quick to react and used his head to send the ball to the right side and putting the Timbers up 3–1, their highest lead of the season so far.
Finally in the 81st minute, Bill Tuiloma would accidentally volley the ball past Jake Gleeson's head and score an own goal.
Sebastián Blanco, Fanendo Adi, and Larrys Mabiala were the goal scorers and Jeff Attinella delivered the Timbers their first clean sheet of the year.
Samuel Armenteros achieved a brace and Diego Valeri moved back into the top goalscorers for the Timbers, tied with Sebastián Blanco at 5.
On June 4, David Guzmán of Costa Rica and Andy Polo of Peru, both made the final 23 man roster for the 2018 FIFA World Cup.
If Portland wins round five they will either travel to LAFC or Sacramento Republic FC depending on that match's outcome.
On June 20, Portland found out they will travel to face Los Angeles FC in the quarterfinal of the 2018 U.S. Open Cup on July 18.
On June 24, Portland resumed play after the MLS 2018 FIFA World Cup break by traveling to Atlanta United FC.
[8] On June 30, Portland traveled to face their rivals Seattle Sounders FC for their first official Cascadia Cup match of the year.
On July 17, Portland signed Argentinian midfielder Tomás Conechny on a 2018 loan with purchase option at the end of the season.
On August 4, Portland defeated Philadelphia Union 3–0 at home with two successfully converted penalties by Diego Valeri and Dairon Asprilla and a goal by David Guzmán.
Portland later that day signed their former 2015 MLS Cup winner left back, Jorge Villafaña from Liga MX side Santos Laguna.
[12] On August 11, Portland lost for the first time at home this season and ended their 15 league unbeaten streak against their rivals, Vancouver Whitecaps FC.
On August 28, Portland loaned out midfielder Eryk Williamson to Portuguese first-division side Clube Desportivo Santa Clara for the club's 2018–19 season with the ability to recall the player in January 2019.
[21] On October 28, Portland traveled to BC Place to play their final Cascadia Cup and league match against Vancouver Whitecaps FC.
At the end of the match, Portland finished eighth for the Supporters' Shield, fifth in the MLS Western Conference, and third in the Cascadia Cup.
Portland is set to play in the 2018 MLS Cup Playoffs knockout round against fourth seed FC Dallas.
On October 31, Portland began its 2018 MLS Cup Playoffs run by traveling to Toyota Stadium where they would face FC Dallas.
On November 4, Portland hosted Seattle Sounders FC for leg one of the 2018 MLS Western Conference Semi-final.
On November 5, left back Jorge Villafaña was called up for U.S. Men's National Team roster for international friendlies against England, Italy.
[22] On November 8, Portland traveled to CenturyLink Field to take on Seattle Sounders FC for the second leg of the 2018 MLS Western Conference Semi-final.
Midfielders Cristhian Paredes (Paraguay) and Andy Polo (Peru) were called up by their respective national teams on November 12.
On November 29, Portland traveled to Children's Mercy Park to finish the second leg of the 2018 MLS Western Conference Final.
Portland will travelled to Mercedes-Benz Stadium to play Atlanta United FC in the 2018 MLS Cup final on December 8, 2018.
On December 8, Portland traveled to Mercedes-Benz Stadium for the 2018 MLS Cup Final against Atlanta United FC where they were defeated 2–0.
Source: [1] Win Draw Loss Upcoming fixture The Timbers and all other MLS clubs join the U.S. Open Cup in round 4.