A 4-1 shootout loss to Juarez on Sunday relegated St Louis to second in the West 3 table, while the Timbers topped West 5 by thumping the Colorado Rapids 4-0.
Match preview
With their place in the next round already assured, we saw a rather cagey affair between St Louis and Juarez last weekend, with the former suffering a narrow defeat.
Despite transitioning to a more possession-based approach under new management, this team had fewer than 50% of the ball in both of their group fixtures.
John Hackworth's men have drawn first blood in three successive matches in all competitions, winning on only one of those occasions (2-1 over Dallas).
On the plus side, though, they have collected points in each Leagues Cup encounter this year and this week can go unbeaten after 90 minutes in at least four consecutive competitive fixtures for just the second time this season.
Friday will be the third one-game knockout match in their history, with St Louis only winning one of those previous encounters, 5-1 over Union Omaha in the 2023 US Open Cup.
Their only victory against the Timbers took place in their inaugural Major League Soccer (MLS) campaign in 2023, claiming a 2-1 triumph.
As we have seen all year long, the Portland Timbers looked unstoppable in the attacking third in the group portion of this tournament.
Phil Neville's men won their two group contests by a combined margin of 6-1, scoring the joint-most goals in the opening round along with DC United.
Portland have scored multiple goals in nine consecutive matches across all competitions, going goalless in just three matches all season.
This upcoming fixture will be their first outside Providence Park in this competition, with the Timbers losing their last two away matches versus MLS opposition.
For as good as they have been in the attacking third this season, defensively, this team have struggled, especially away from home, conceding in all but two league fixtures this year as the visitors.
Portland have never lost an away contest against St Louis City, playing to a 0-0 draw earlier this season and winning 2-1 in their first visit to CityPark in 2023.
St Louis City Leagues Cup form:
W
L
St Louis City form (all competitions):
L
L
L
D
W
L
Portland Timbers Leagues Cup form:
W
W
Portland Timbers form (all competitions):
L
W
W
L
W
W
Team News
Against Juarez, St Louis were missing Joakim Nilsson with a knock, Joao Klauss and Rasmus Alm were sidelined with knee injuries, Celio Pompeu sat out due to a sore leg and Tomas Ostrak is done for the season after undergoing ankle tendon surgery.
On Saturday, the club traded defender Tim Parker and General Allocation Money to the New England Revolution in exchange for Henry Kessler and also added Jannes Horn from FC Nurnberg in Bundesliga 2.
Simon Becher scored his first goal as a member of St Louis City, though their lead lasted a mere four minutes, while Cedric Teuchert and Marcel Hartel missed from the penalty spot.
The Timbers were without Marvin Loria versus Colorado because of a knee injury, with Juan David Mosquera, Miguel Araujo, Claudio Bravo, Cristhian Paredes and David Ayala being the new faces in the starting 11.
Earlier this week, the club mutually parted ways with French defender Larrys Mabiala, who had spent eight seasons with Portland.
Antony got the ball rolling for the Timbers last Thursday with his first of the tournament, with Ayala and Santiago Moreno adding some insurance, while Mason Toye scored his first as a Timber.
St Louis City possible starting lineup:
Burki; Nerwinski, Yaro, Hiebert, Markanich; Durkin, Lowen; Vassilev, Blom, Hartel; Becher
Portland Timbers possible starting lineup:
Crepeau; E. Miller, Zuparic, K. Miller, Bravo; Paredes, Williamson; Antony, Evander, Rodriguez; Mora
We say: St Louis City 1-4 Portland Timbers
We believe there is too much firepower on the Timbers side for St Louis to handle as the home side are still in a transitional period, learning to play out from the back.