42 teams between the USL Championship and USL League One are contesting this season’s USL Cup, an inter-league tournament that begins with a group stage before winnowing the field down to an eight-team knockout.
Which clubs are truly in the mix to advance and compete for silverware? That’s what we’re here to find out.
After a jam-packed opening weekend to the 2026 tournament, the competitive landscape has begun to come together. To sort through the 20-match slate and see where everyone lands, I’m ranking every entrant, breaking down what went right or wrong on Saturday in the group openers, and separating the true USL Cup contenders to the also-rans.
Let’s dig in.
1. Tampa Bay Rowdies
Result: 2-0 win v. Sarasota
To call Tampa Bay’s lineup in their USL Cup opener a “B” team would be unduly harsh, but it’s not entirely wrong. Super subs Evan Conway, Karsen Henderlong, and Mattheus Oliveira all got rare starts in the attacking corps; teenaged Alex Rodriguez held down the right back spot. Given how dominant the Rowdies looked against visiting Sarasota, you’d be forgiven for thinking Dom Casciato went all-out.
Tampa Bay stuck to their usual 4-2-2-2 offensively, and interchange was rampant. Mattheus was everywhere across the attacking midfield, and Conway mixed sharp box runs with a solid presence in the halfspace. Those patterns gradually drew Paradise’s back three out of alignment, opening space for devastating overlaps from Rodriguez and left-sided Charlie Ostrem.
31’ | Karsen bags his first in Green & Gold to open the night! #TBRvSRQ | 1-0
— Tampa Bay Rowdies (@tampabayrowdies.bsky.social) 2026-04-26T00:23:39.212Z
Tampa Bay’s go-ahead effort was driven by interplay in that manner, with Lewis Hilton taking an opportunity to bounce his way upfield from the No. 6 spot. Doing so forced a defender to step, thus breaking Sarasota’s shape and creating a sense of numerical parity in the box. When a shot arrived and a rebound resulted, Henderlong – who nabbed a brace against the League One side – was ready to pounce.
