| First Round | Away Team | Result | Home Team | ||
| June 9 | Sonoma County Sol (USASA) | 5:2 | Orange County Blue Star (PDL) | ||
| June 9 | Richmond Kickers (USL-2) | 1:2 | Carolina RailHawks (USL-1) | ||
| June 9 | Emigrantes Das Ilhas (USASA) | 2:3 (AET) | Western Mass Pioneers (USL-2) | ||
| June 9 | Charlotte Eagles (USL-2) | 0:2 | Wilmington Hammerheads (USL-2) | ||
| June 9 | Pittsburgh Riverhounds (USL-2) | 1:1 (2:4 PK) | Rochester Rhinos (USL-1) | ||
| June 9 | St. Louis Lions (PDL) | 0:3 | Cleveland City Stars (USL-1) | ||
| June 9 | Bavarian SC (USASA) | 1:3 | Chicago Fire (PDL) | ||
| June 9 | Reading Rage (PDL) | 1:4 | Harrisburg City Islanders (USL-2) | ||
| June 9 | 402 (USASA) | 2:3 | Minnesota Thunder (USL-1) | ||
| June 9 | Atlanta FC (USASA) | 0:2 | Charleston Battery (USL-1) | ||
| June 9 | Lynch’s FC (USASA) | 1:2 | Miami FC Blues (USL-1) | ||
| June 9 | Mississippi Brilla (PDL) | 0:2 | Austin Aztex (USL-1) | ||
| June 9 | Arizona Sahuaros (USASA) | 1:2 | El Paso Patriots (PDL) | ||
| June 9 | Portland Timbers (USL-1) | 3:0 | Kitsap Pumas (PDL) | ||
| June 10 | Aegean Hawks FC (USASA) | 0:1 | Real Maryland Monarchs (USL-2) | ||
| June 10 | Crystal Palace Baltimore (USL-2) | 0:3 | Ocean City Barons (PDL) | ||
| Second Round | Away Team | Result | Home Team | ||
| June 16 | Real Maryland Monarchs (USL-2) | 0-1 (AET) | Ocean City Barons (PDL) | ||
| June 16 | Wilmington Hammerheads (USL-2) | 3:3 (4:3 PK) | Carolina RailHawks (USL-1) | ||
| June 16 | Cleveland City Stars (USL-1) | 1:2 (AET) | Rochester Rhinos (USL-1) | ||
| June 16 | Western Mass Pioneers (USL-2) | 0:0 (3:4 PK) | Harrisburg City Islanders (USL-2) | ||
| June 16 | Charleston Battery (USL-1) | 1:0 | Miami FC Blues (USL-1) | ||
| June 16 | Chicago Fire (PDL) | 0:4 | Minnesota Thunder (USL-1) | ||
| June 16 | El Paso Patriots (PDL) | 0:2 | Austin Aztex (USL-1) | ||
| June 16 | Portland Timbers (USL-1) | 3:0 | Sonoma County Sol (USASA) | ||
| Third Round | Away Team | Result | Home Team | ||
| June 30 | Columbus Crew (MLS) | 1:1 (3:5 PK) | Rochester Rhinos (USL-1) | ||
| June 30 | Chicago Fire (MLS) | 0:1 | Wilmington Hammerheads (USL-2) | ||
| June 30 | Harrisburg City Islanders (USL-2) | 2:1 (AET) | New England Revolution (MLS) | ||
| June 30 | Ocean City Barons (PDL) | 0:2 | DC United (MLS) | ||
| June 30 | Chivas USA (MLS) | 1:3 | Charleston Battery (USL-1) | ||
| June 30 | Kansas City Wizards (MLS) | 3:3 (4:2 PK) | Minnesota Thunder (USL-1) | ||
| July 1 | Houston Dynamo (MLS) | 2:0 | Austin Aztex (USL-1) | ||
| July 1 | Seattle Sounders FC (MLS) | 2:1 | Portland Timbers (USL-1) | ||
| Quarterfinals | Away Team | Result | Home Team | ||
| July 7 | Wilmington Hammerheads (USL-2) | 1:2 | Rochester Rhinos (USL-1) | ||
| July 7 | Harrisburg City Islanders (USL-2) | 1:2 | DC United (MLS) | ||
| July 7 | Houston Dynamo (MLS) | 4:0 | Charleston Battery (USL-1) | ||
| July 7 | Kansas City Wizards (MLS) | 0:1 | Seattle Sounders (MLS) | ||
| Semifinals | Away Team | Result | Home Team | ||
| July 21 | Rochester Rhinos (USL-1) | 1:2 | DC United (MLS) | ||
| July 21 | Houston Dynamo (MLS) | 1:2 (AET) | Seattle Sounders (MLS) | ||
| Final (RFK Stadium – Washington DC) | |||||
| September 2 | Seattle Sounders (MLS) | 2:1 | 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) | |||||