The Colorado Rapids are back in the US Open Cup quarter-finals for the first time since 2006, and they will try to turn that into something they have not reached since 1999: a semi-final berth. San Jose Earthquakes visit on Wednesday May 20 at 8:00 p.m. MST in a meeting that gives Colorado its first MLS opponent of the tournament.

That matters because the Rapids have never won the US Open Cup, and neither have the Earthquakes. Colorado reached this stage by beating the Colorado Springs Switchbacks in the Round of 16 after 120 minutes and penalties, a night that swung from a late red card for Kosi Thompson to a last-gasp Switchbacks penalty that dragged the match into a shootout. Georgi Minoungou appeared to have won it in extra time before the finish unraveled, and Keegan Rosenberry delivered the decisive penalty to send the Rapids through.

San Jose arrives with a very different path to this point. The Earthquakes beat Phoenix Rising 2-0 and Minnesota United 4-2 in the US Open Cup, part of a run that began with 11 wins in their first 12 games across all competitions. That start looked like the kind of form that could carry them deep into the spring, but they have gone four games without a win in MLS since the Minnesota result, with schedule congestion also cited as part of the burden on the group.

The matchup also reaches back into Colorado's own history. The Rapids beat the Earthquakes at home en route to their only trophy, a reminder that this club has been close to this competition before without ever getting over the line. San Jose, another MLS original, has the same drought. Both sides are chasing a first Open Cup title, but Colorado has the cleaner route into Wednesday's tie after surviving a knockout round that nearly slipped away against lower-league opposition.

The timing gives the game an edge beyond the bracket. With the quarter-final arriving after Colorado's penalty escape and San Jose's recent wobble in league play, the winner will leave with more than a place in the next round. The Rapids would move within one game of matching their deepest Open Cup run in a quarter-century, while San Jose would have to steady itself quickly to keep its early-season promise from fading. The match will be available on Paramount Plus, CBS Sports Network and Fubo Sports.