| First Round | Away Team | Result | Home Team | ||
| June 10 | Yakima Reds (PDL) | 1:5 | Harrisburg City Islanders (USL-2) | ||
| June 10 | Boston Olympiakos (USASA) | 0:2 | Western Mass Pioneers (USL-2) | ||
| June 10 | Fredericksburg Gunners (PDL) | 0:3 | Richmond Kickers (USL-2) | ||
| June 10 | Crystal Palace Baltimore (USL-2) | 2:1 | Los Angeles Legends (PDL) | ||
| June 10 | RWB Adria (USASA) | 1:2 (AET) | Rochester Rhinos (USL-1) | ||
| June 10 | Pittsburgh Riverhounds (USL-2) | 4:0 | AAC Eagles (USASA) | ||
| June 10 | St. Louis Lions (PDL) | 1:4 | Minnesota Thunder (USL-1) | ||
| June 10 | Cleveland City Stars (USL-1) | 2:1 | Michigan Bucks (PDL) | ||
| June 10 | Bradenton Academics (PDL) | 2:4 | Miami FC (USL-1) | ||
| June 10 | Atlanta Silverbacks (USL-1) | 2:2 (5:4 PKs) | Austin Aztex U23s (PDL) | ||
| June 10 | Clearwater Galactics (USASA) | 2:5 | Charlotte Eagles (USL-2) | ||
| June 10 | Seattle Sounders (USL-1) | 1:0 (AET) | Arizona Sahuaros (USASA) | ||
| June 10 | Hollywood United (USASA) | 3:2 | Portland Timbers (USL-1) | ||
| June 10 | Brooklyn Knights (PDL) | 0:1 | Carolina RailHawks (USL-1) | ||
| June 10 | ASC New Stars (USASA) | 0:3 | Charleston Battery (USL-1) | ||
| June 13 | NY Pancyprian Freedoms (USASA) | 2:3 (AET) | Real Maryland Monarchs (USL-2) | ||
| Second Round | Away Team | Result | Home Team | ||
| June 24 | Cleveland City Stars (USL-2) | 2:0 | Minnesota Thunder (USL-1) | ||
| June 24 | Crystal Palace Baltimore (USL-2) | 2:2 (3:1 PKs) | Harrisburg City Islanders (USL-2) | ||
| June 24 | Richmond Kickers (USL-2) | 2:1 | Western Mass Pioneers (USL-2) | ||
| June 24 | Real Maryland Monarchs (USL-2) | 0:1 | Carolina RailHawks (USL-1) | ||
| June 24 | Pittsburgh Riverhounds (USL-2) | 0:3 | Rochester Rhinos (USL-1) | ||
| June 24 | Charlotte Eagles (USL-2) | 1:2 | Charleston Battery (USL-1) | ||
| June 24 | Atlanta Silverbacks (USL-1) | 0:1 | Miami FC (USL-1) | ||
| June 24 | Hollywood United (USASA) | 0:6 | Seattle Sounders (USL-1) | ||
| Third Round | Away Team | Result | Home Team | ||
| July 1 | Richmond Kickers (USL-2) | 0:3 | New England Revolution (MLS) | ||
| July 1 | Houston Dynamo (MLS) | 1:1 (3:4 PKs) | Charleston Battery (USL-1) | ||
| July 1 | New York Red Bulls (MLS) | 0:2 | Crystal Palace Baltimore (USL-2) | ||
| July 1 | Kansas City Wizards (MLS) | 4:2 (AET) | Carolina RailHawks (USL-1) | ||
| July 1 | Rochester Rhinos (USL-1) | 0:2 | DC United (MLS) | ||
| July 1 | Cleveland City Stars (USL-1) | 1:4 | Chicago Fire (MLS) | ||
| July 1 | Miami FC (USL-1) | 1:2 | FC Dallas (MLS) | ||
| July 1 | Chivas USA (MLS) | 0:2 | Seattle Sounders (USL-1) | ||
| Quarterfinals | Away Team | Result | Home Team | ||
| July 8 | Crystal Palace Baltimore (USL-2) | 1:1 (3:5 PKs) | New England Revolution (MLS) | ||
| July 8 | Chicago Fire (MLS) | 1:2 (AET) | DC United (MLS) | ||
| July 8 | Charleston Battery (USL-1) | 3:1 | FC Dallas (MLS) | ||
| July 8 | Kansas City Wizards (MLS) | 0:0 (5:6 PKs) | Seattle Sounders (USL-1) | ||
| Semifinals | Away Team | Result | Home Team | ||
| August 12 | New England Revolution (MLS) | 1:3 | DC United (MLS) | ||
| August 12 | Seattle Sounders (USL-1) | 1:1 (3:4 PKs) | Charleston Battery (USL-1) | ||
| Final (RFK Stadium – Washington DC) | |||||
| September 3 | Charleston Battery (USL-1) | 1:2 | DC United (MLS) | ||
| Division 1 | Major League Soccer (MLS) | AET | After Extra Time | ||
| Division 2 | USL First Division (USL-1) | PKs | Penalty Kicks | ||
| Division 3 | USL Second Division (USL-2) | ||||
| Division 4 | Premier Development League (PDL) | ||||
| US Adult Soccer Assoc. (USASA) | |||||