Here are five thoughts on the slate that awaits the club in 2020.
After last year's season-opening ten game road trip and season-closing stretch in which they played 11 of their final games at home, the Timbers' 2020 schedule is a return to normalcy. The club's longest homestand this season will be just two games. Their longest roadtrip will be just three, and includes a midweek match.
It's a breath of fresh air. The long roadtrip to begin last year was extremely trying, as the Timbers took just one point from their first six games, and the glut of home games to finish the season proved almost equally challenging.
It is safe to say already that there will be entirely less focus on the schedule this year — which no one, either inside the club or outside of it, will regret.
For the first time since they entered MLS in 2011, the Timbers will not face every other club in the league.
With the additions of Nashville and Inter Miami, MLS will have have 26 teams this season — making it impossible for each club to play all of the teams in their conference twice and all of the teams in the opposing conference once within 34 games.
So while the Timbers will still face each Western Conference side home and away, they will only play ten of the Eastern Conference's 13 teams — avoiding meetings with DC United, New York City FC, and the Montreal Impact.
On first glance, this should work out relatively well for the Timbers. NYCFC was the Eastern Conference's best team last season, while DC was a playoff team as well.
3. Midweek Games
Because of how backloaded their schedule was last season, the Timbers played five midweek games — four of which were at home — from June through October.
This year, the schedule is spaced much more kindly: the Timbers will only play three midweek games in total — at Chicago in May, at home against Colorado in June, and at home against Columbus to kick off July.
The club will have midweek U.S. Open Cup committments as well, more if they advance in that competition, but the spacing of their league schedule should mean less squad rotation and a fresher group down the stretch than we saw last year.
4. Caleb Porter Returns
Because he took over an Eastern Conference club, and because that club was largely irrelevant last year, there was very little discussion of Caleb Porter in Timbers circles last year.
Portland got its first win of the season in Ohio against Porter's Columbus Crew team in April, and traded David Guzmán to the Crew shortly thereafter, but that was it for overlap between Porter's new team and his old one.
This year, that will change. Porter is set to make his debut as an opposing manager at Providence Park on July 1, and he will have Darlington Nagbe, acquired via trade with Atlanta in November, in tow.
It will be fascinating to see what kind of reception Porter gets. He is the Timbers' only title-winning coach and the man who in many ways led the club into the upper echelon of MLS, but very few supporters have voiced any ongoing regret over his shocking decision to resign more than two years ago.
5. Zarek Valentin Returns
Excited as a number of fans will be to see the club's longest-tenured manager come back to Providence Park, the most eagerly anticipated return of an ex-Timber this year will no doubt be that of Zarek Valentin: the fan favorite fullback who was selected by Nashville in the Expansion Draft and then traded to Houston.
Valentin, who played for Porter at Akron, made 98 MLS appearances across four seasons with the Timbers and became one of the club's most visible faces — outspoken on social issues, generous in the community, and deeply appreciated for his hard work and intelligence on the field.
His new club, under the leadership of first year manager Tab Ramos, will travel to Providence Park for a Saturday night clash on July 25th. If Valentin is in the starting lineup, expect him to the biggest ovation an opposing player has received in years.