August 1, 202010:04PM EDT

We're down to the final four in the MLS is Back Tournament Knockout Stage presented by Audi.

The semifinals will be played midweek on Wednesday, August 5 and Thursday, August 6 and the winners will face off in the final on Tuesday, August 11, when one team will walk away with a Concacaf Champions League place, a trophy and chunk of prize money to boot. 

Semifinal matchups

Here's a more in-depth look at how each semifinal shapes up:

Philadelphia Union vs. Portland Timbers

Wednesday, August 5 (8 pm ET | FS1, TUDN, UniMás in US; TSN, TVAS2 in Canada)

It’s a battle of the young guns vs. the old reliables in one MLS is Back Tournament semifinal as the Portland Timbers and Philadelphia Union will meet to decide the first finalist on Wednesday. The Union have been buoyed by academy stars Brenden Aaronson and Mark McKenzie — in addition to some superb finishing from Sergio Santos and Alejandro Bedoya’s leadership — in their run to the semifinals. The Timbers’ MVP has been 32-year-old Sebastian Blanco, who has two goals and five assists in the tournament, while Timbers legends Diego Valeri and Diego Chara are still going strong as Valeri was shifted to bench role in the quarterfinals. But don’t let anyone tell you Portland are lacking youth, as 23 year olds Jeremy Ebobisse and Eryk Williamson have broken out in Orlando.

Philadelphia Union: The Union have emerged as one of the favorites, but a prevailing theme throughout the tournament before their quarterfinal clash with SKC was a feeling they had yet to really hit their stride. That changed against Sporting, as they raced out to a 3-0 lead in the space of 15 minutes in the first half and did well to withstand some second-half pressure, protect the lead, and see out the victory. That’s the type of thing this team is capable of when they’re on, and Philly will hope the strong showing in the quarters is a sign they’re peaking at the right time.

Portland Timbers: One of the most impressive teams during the group stage, the Timbers had to grind out 90 minutes against a defensive FC Cincinnati side before advancing in a penalty-kick shootout. Despite a controversial penalty that gave NYCFC an early penalty, Portland were able to bounce back behind Blanco and Valeri off the bench to roll to a 3-1 win over the Cityzens. After a frustrating end to their 2019 season, it appears the Timbers have been rejuvenated in Orlando.

Series history: Portland have dominated the series against the Union, winning six of the 10 matchups between the clubs. Philadelphia’s only win came back in 2015. Valeri — who may have shifted to a supersub role — has a goal and an assist in each of his last two matches against Philly.

FiveThirtyEight Projection to advance: Philadelphia 57%, Portland 43%

Orlando City SC vs. Minnesota United FC

Thursday, August 6 (8 pm ET | ESPN2, ESPN Deportes in US; TSN, TVAS2 in Canada)

The Adrian Heath Derby will decide one of the spots in the MLS is Back Tournament final. Minnesota United FC and Orlando City SC will meet on Thursday in the second of the two semifinals, as Loons head coach Adrian Heath will face off against his old team. The Englishman was part of the Orlando organization since it’s inception, leading them to two USL titles. He lasted just one-and-a-half seasons with the Lions in MLS before he and the club decided to part ways. Orlando’s best season in MLS came under Heath in their inaugural campaign back in 2015. Neither Orlando or Minnesota, who Heath has coached since the club joined MLS in 2017, has won a trophy as an MLS club.

Orlando City SC: Orlando City continued what has been a remarkable run with their penalty kick shootout triumph over mighty LAFC. It might still be too early to declare the Lions fully arrived, but they earned their victory over the reigning Supporters’ Shield champs and seem to have a magic about them in this tournament. It’s the continuation of an admirable job from new head coach Oscar Pareja, who seems to have the players fully bought in on his philosophy and identity in a remarkably short time. They’ve looked the part of a legit contender, with a talented and cohesive attack and a defense that looks much improved over the leaky units of year’s past. 

Minnesota United FC: The perpetual underdogs enter Thursday’s match flying high. Though they have not been favored in either of their Knockout Stage matches, the Loons have been unable to jump out ahead in both matches. Against Columbus, they had to go into a penalty-kick shootout to advance, but their quarterfinal match against the San Jose Earthquakes was a much different story. After goals in the 20th and 21st minutes, Minnesota cruised to a 4-1 in over the Quakes to book their place in their semis.

Series history: Orlando have yet to beat Heath and the Loons as Minnesota have won two of the three meetings between the clubs, with the third being a 1-1 draw at Allianz Field last season.

FiveThirtyEight Projection to advance: Minnesota 54%, Orlando 46%