| First Round | Away Team | Result | Home Team | |
| June 9 | Olympia Stamford (USASA) | 1:4 | Seattle Sounders Select (PDL) | |
| June 9 | Mexico SC (USASA) | 1:1 (4:5 PKs) | Central Coast Roadrunners (PDL) | |
| June 13 | Uruguay SC (USASA) | 3:2 | Miami Strike Force (PDL) | |
| June 13 | Chaldean Arsenal (USASA) | 0:3 | Mid-Michigan Bucks (PDL) | |
| Second Round | Away Team | Result | Home Team | |
| June 26 | Tampa Bay Mutiny (MLS) | 2:3 | Connecticut Wolves (A-League) | |
| June 27 | Chico Rooks (D3 Pro) | 3:4 | El Paso Patriots (A-League) | |
| June 27 | Colorado Rapids (MLS) | 0:2 | Pittsburgh Riverhounds (A-League) | |
| June 27 | Seattle Sounders (A-League) | 0:4 | Kansas City Wizards (MLS) | |
| June 27 | San Diego Flash (A-League) | 0:3 | Chicago Fire (MLS) | |
| June 27 | Utah Blitzz (D3 Pro) | 0:2 | Milwaukee Rampage (A-League) | |
| June 27 | San Jose Earthquakes (MLS) | 6:0 | Central Coast Roadrunners (PDL) | |
| June 27 | Nashville Metros (A-League) | 0:5 | Los Angeles Galaxy (MLS) | |
| June 27 | Seattle Sounders Select (PDL) | 3:2 (ASDET) | Dallas Burn (MLS) | |
| June 27 | Metrostars (MLS) | 1:4 | Charleston Battery (A-League) | |
| June 27 | Mid-Michigan Bucks (PDL) | 1:7 | New England Revolution (MLS) | |
| June 27 | Carolina Dynamo (D3 Pro) | 1:5 | Columbus Crew (MLS) | |
| June 27 | Miami Fusion (MLS) | 4:0 | Uruguay SC (USASA) | |
| June 27 | Reading Rage (D3 Pro) | 2:7 | Richmond Kickers (A-League) | |
| June 27 | New Jersey Stallions (D3 Pro) | 0:8 | DC United (MLS) | |
| July 2 | Hershey Wildcats (A-League) | 1:0 | Rochester Raging Rhinos (A-League) | |
| Third Round | Away Team | Result | Home Team | |
| July 11 | Pittsburgh Riverhounds (A-League) | 2:1 | El Paso Patriots (A-League) | |
| July 11 | Chicago Fire (MLS) | 1:0 | Kansas City Wizards (MLS) | |
| July 11 | San Jose Earthquakes (MLS) | 0:0 (7:6 PKs) | Milwaukee Rampage (A-League) | |
| July 11 | Seattle Sounders Select (PDL) | 1:3 | Los Angeles Galaxy (MLS) | |
| July 11 | Charleston Battery (A-League) | 1:2 | New England Revolution (MLS) | |
| July 11 | Miami Fusion (MLS) | 1:2 | Columbus Crew (MLS) | |
| July 11 | Connecticut Wolves (A-League) | 1:2 | Richmond Kickers (A-League) | |
| July 11 | Hershey Wildcats (A-League) | 0:3 | DC United (MLS) | |
| Quarterfinals | Away Team | Result | Home Team | |
| July 24 | Pittsburgh Riverhounds (A-League) | 2:3 (ASDET) | Chicago Fire (MLS) | |
| July 24 | Los Angeles Galaxy (MLS) | 1:1 (10:9 PKs) | San Jose Earthquakes (MLS) | |
| July 24 | Columbus Crew (MLS) | 1:2 | New England Revolution (MLS) | |
| July 24 | Richmond Kickers (A-League) | 1:2 | DC United (MLS) | |
| Semifinals | Away Team | Result | Home Team | |
| August 22 | DC United (MLS) | 0:2 | New England Revolution (MLS) | |
| August 22 | Chicago Fire (MLS) | 0:1 (ASDET) | Los Angeles Galaxy (MLS) | |
| Final (Titan Stadium – Fullerton, Calif.) | ||||
| October 27 | New England Revolution (MLS) | 1:2 (ASDET) | Los Angeles Galaxy (MLS) | |
| ———————- | ||||
| Division 1 | Major League Soccer (MLS) | ASDET | After Sudden Death Extra Time | |
| Division 2 | A-League | PKs | Penalty Kicks | |
| Division 3 | D3 Pro League (D3 Pro) | |||
| Division 4 | Premier Development League (PDL) | |||
| US Amateur Soccer Assoc. (USASA) | ||||