[1] Portland also announced roster moves that include recalling Eryk Williamson's loan from Portuguese first-division side Clube Desportivo Santa Clara.
Portland exercised contract options on goalkeeper Kendall McIntosh, defenders Modou Jadama and Bill Tuiloma, and forwards Jeremy Ebobisse and Foster Langsdorf.
Portland did not exercise contract options on midfielders Victor Arboleda, Tomás Conechny, Andrés Flores and Lawrence Olum.
[8] On December 27, Portland traded right back Alvas Powell to Major League Soccer side FC Cincinnati for $250,000 in General Allocation Money.
[12] On January 11, Portland selected American forward Ryan Sierakowski from Michigan State and German defender Lennart Hein from Saint Louis University in the first two rounds of the 2019 MLS SuperDraft.
[13] On January 14, Portland selected American defender Francesco Moore from Indiana and Venezuelan midfielder David Zalzman from Memphis in the final third and forth rounds of the 2019 MLS SuperDraft.
On February 13, Portland began renegotiation terms of their deal with NK Olimpija Ljubljana on goalkeeper Aljaž Ivačič, after he was found to have a leg injury.
[25] On February 20, Portland signed Paraguayan right back Jorge Moreira on loan from Argentine Primera División side River Plate with purchase option.
[27] On February 23, Portland defeated Real Salt Lake 3–0 in their final preseason match in the 2019 Mobile Mini Sun Cup.
Additionally, forward Jeremy Ebobisse, defender Marco Farfan and midfielder Eryk Williamson have been named to the U.S. U-23 Men's National Team.
Guerrero defeated San Jose Earthquakes Alan "CaliSCG" Ortega with a 3–1 win in the knockout round but fell to FC Dallas' AlanAvi in the 2019 eMLS Cup Western Conference Semifinals with a score of 1–0.
[32] On May 6, Portland traded defensive midfielder David Guzmán to Columbus Crew SC in exchange for a 2019 international roster slot.
[33] Shortly after, Portland announced the signing of their new Designated Player, Argentine forward Brian Fernández from Mexican club Necaxa.
On May 20, midfielder Andrés Flores was announced as a preliminary pick to the El Salvador national team for the 2019 CONCACAF Gold Cup.
[35] On May 21, midfielder Eryk Williamson was announced to the U.S. Senior and U-23 Men's National Team preparation camp from May 26 to June 2 in Annapolis, Maryland.
On May 30, it was announced that Portland will travel to Tacoma, Washington where they will face Seattle Sounders FC at Cheney Stadium for the fourth round of the 2019 U.S. Open Cup.
On June 1, Portland hosted Los Angeles FC in front of a Providence Park record crowd of 25,218 for their home opener for the 2019 season.
[38] On June 12, Portland traveled to Tacoma, Washington to play their first 2019 U.S. Open Cup match against Seattle Sounders FC in the fourth round at Cheney Stadium.
Portland advanced with a 2–1 victory with both goals scored by Brian Fernández, assisted by Diego Valeri, Sebastián Blanco, and Jeremy Ebobisse.
Diego Chará was selected by Orlando City SC head coach James O'Connor to participate in the 2019 MLS All-Star game on July 29 against Atlético Madrid.
With a mixed roster, Portland were defeated 1–2 with the only goal scorer being Tomás Conechny, assisted by Julio Cascante and Marvin Loría.
On July 2, Portland announced the multiyear contract extensions of coaching staff members Giovanni Savarese, Carlos Llamosa, Miles Joseph, Guillermo “Memo” Valencia and Shannon Murray.
On July 29, Portland's secondary goalkeeper Jeff Attinella underwent successful surgery to repair anterior labrum tear in right shoulder.
During the final minutes of stoppage time, Minnesota was awarded a penalty after a VAR review citing Larrys Mabiala with a handball in the box.
On August 7, Portland's 2019 U.S. Open Cup run came to an end as they were defeated 2–1 by Minnesota United FC with the lone goal being scored by Brian Fernández (assisted by Jeremy Ebobisse) in the 45+2 minute.
Portland defeated Chicago 3–2 after Fire midfielder Aleksandar Katai was sent off for a high elbow on Julio Cascante in the half hour mark.
On August 23, Portland hosted their rivals, Seattle Sounders FC to the final Cascadia Cup regular season meeting of the year.
Portland's supporters, the Timbers Army performed a silent protest until the 33rd minute, showing their upset on the Iron Front ban.
Andrés Flores was called up by El Salvador for CONCACAF Nations League matches against St. Lucia and the Dominican Republic on September 7 and 10.
On October 6, Portland hosted and defeated San Jose Earthquakes with a score of 3–1 for their final regular season match, granting them entry into the 2019 MLS Cup Playoffs.