| First Round | Away Team | Result | Home Team | |
| June 4 | Bridgeport Italians (USASA) | 0:1 (Forfeit) | Chesapeake Dragons (PDL) | |
| June 4 | Chico Rooks (USASA) | 0:1 | Fresno Fuego (PDL) | |
| June 5 | Bavarian SC (USASA) | 2:1 (ASDET) | Des Moines Menace (PDL) | |
| June 6 | DS United (USASA) | 1:4 | Raleigh CASL Elite (PDL) | |
| Second Round | Away Team | Result | Home Team | |
| June 24 | Reading Rage (PSL) | 0:1 | Bavarian SC (USASA) | |
| June 24 | Bradenton Academics (PDL) | 1:2 (ASDET) | Wilmington Hammerheads (PSL) | |
| June 24 | Long Island Rough Riders (PSL) | 1:2 | Mid-Michigan Bucks (PDL) | |
| June 24 | Raleigh CASL Elite (PDL) | 1:2 | Carolina Dynamo (PSL) | |
| June 24 | Utah Blitzz (PSL) | 0:4 | Fresno Fuego (PDL) | |
| July 10 | Chesapeake Dragons (PDL) | 2:3 (ASDET) | New Hampshire Phantoms (PSL) | |
| Third Round | Away Team | Result | Home Team | |
| July 16 | Atlanta Silverbacks (A-League) | 1:2 | Wilmington Hammerheads (PSL) | |
| July 16 | Carolina Dynamo (PSL) | 0:5 | Virginia Beach Mariners (A-League) | |
| July 16 | Metrostars (MLS) | 4:0 | Mid-Michigan Bucks (PDL) | |
| July 16 | New Hampshire Phantoms (PSL) | 1:4 | Rochester Raging Rhinos (A-League) | |
| July 16 | Pittsburgh Riverhounds (A-League) | 1:2 | DC United (MLS) | |
| July 16 | Seattle Sounders (A-League) | 1:0 | Minnesota Thunder (A-League) | |
| July 22 | Fresno Fuego (PDL) | 5:2 | El Paso Patriots (A-League) | |
| July 23 | Bavarian SC (USASA) | 1:4 | Milwaukee Wave United (A-League) | |
| Fourth Round | Away Team | Result | Home Team | |
| August 5 | San Jose Earthquakes (MLS) | 0:1 | Seattle Sounders (A-League) | |
| August 5 | Kansas City Wizards (MLS) | 2:3 | Colorado Rapids (MLS) | |
| August 6 | Virginia Beach Mariners (A-League) | 0:1 (ASDET) | DC United (MLS) | |
| August 6 | Fresno Fuego (PDL) | 1:3 | Los Angeles Galaxy (MLS) | |
| August 6 | Dallas Burn (MLS) | 1:4 | Wilmington Hammerheads (PSL) | |
| August 6 | Chicago Fire (MLS) | 4:1 | Milwaukee Wave United (A-League) | |
| August 6 | Metrostars (MLS) | 4:3 | Columbus Crew (MLS) | |
| August 6 | Rochester Raging Rhinos (A-League) | 1:2 | New England Revolution (MLS) | |
| Quarterfinals | Away Team | Result | Home Team | |
| August 27 | Los Angeles Galaxy (MLS) | 5:1 | Seattle Sounders (A-League) | |
| August 27 | DC United (MLS) | 1:0 | Wilmington Hammerheads (PSL) | |
| August 27 | Colorado Rapids (MLS) | 1:2 | Chicago Fire (MLS) | |
| August 27 | New England Revolution (MLS) | 1:2 (ASDET) | Metrostars (MLS) | |
| Semifinals | Away Team | Result | Home Team | |
| September 23 | Los Angeles Galaxy (MLS) | 2:3 | Chicago Fire (MLS) | |
| October 1 | DC United (MLS) | 2:3 | Metrostars (MLS) | |
| Final (Giants Stadium – East Rutherford, NJ) | ||||
| October 15 | Chicago Fire (MLS) | 1:0 | Metrostars (MLS) | |
| ———————- | ||||
| Division 1 | Major League Soccer (MLS) | ASDET | After Sudden Death Extra Time | |
| Division 2 | A-League | PKs | Penalty Kicks | |
| Division 3 | Pro Soccer League (PSL) | |||
| Division 4 | Premier Development League (PDL) | |||
| US Adult Soccer Assoc. (USASA) | ||||