| First Round | Away Team | Result | Home Team | |
| June 5 | Los Lobos (USASA) | 1:8 | Wilmington Hammerheads (D3 Pro) | |
| June 8 | Austin Lone Stars (D3 Pro) | 2:3 | Mid-Michigan Bucks (PDL) | |
| June 9 | New York Freedoms (PDL) | 3:1 | Cape Cod Crusaders (D3 Pro) | |
| June 9 | United German Hungarians (USASA) | 2:1 | New Jersey Stallions (D3 Pro) | |
| June 10 | Cocoa Expos (PDL) | 5:3 | Northern Virginia Royals (D3 Pro) | |
| June 11 | Mexico SC (USASA) | 2:3 (ASDET) | Arizona Sahuaros (D3 Pro) | |
| June 16 | Spokane Shadow (PDL) | 3:2 (ASDET) | Chico Rooks (D3 Pro) | |
| June 20 | Bavarian SC (USASA) | 0:1 | Carolina Dynamo (D3 Pro) | |
| Second Round | Away Team | Result | Home Team | |
| June 23 | United German Hungarians (USASA) | 0:7 | Staten Island Vipers (A-League) | |
| June 23 | Mid-Michigan Bucks (PDL) | 2:1 | Minnesota Thunder (A-League) | |
| June 23 | Spokane Shadow (PDL) | 1:3 | Seattle Sounders (A-League) | |
| June 30 | New York Freedoms (PDL) | 1:2 (ASDET) | Rochester Raging Rhinos (A-League) | |
| June 30 | Arizona Sahuaros (D3 Pro) | 2:9 | San Diego Flash (A-League) | |
| July 6 | Carolina Dynamo (D3 Pro) | 2:0 | Orange County Zodiac (A-League) | |
| July 6 | Wilmington Hammerheads (D3 Pro) | 1:2 | Charleston Battery (A-League) | |
| July 10 | Jacksonville Cyclones (A-League) | 7:2 | Cocoa Expos (PDL) | |
| Third Round | Away Team | Result | Home Team | |
| July 12 | Tampa Bay Mutiny (MLS) | 2:1 | Mid-Michigan Bucks (PDL) | |
| July 13 | Staten Island Vipers (A-League) | 3:2 (ASDET) | Metrostars (MLS) | |
| July 13 | Carolina Dynamo (D3 Pro) | 0:3 | Columbus Crew (MLS) | |
| July 13 | Jacksonville Cyclones (A-League) | 0:3 | Dallas Burn (MLS) | |
| July 13 | Seattle Sounders (A-League) | 0:1 | Colorado Rapids (MLS) | |
| July 14 | Chicago Fire (MLS) | 0:1 | Rochester Raging Rhinos (A-League) | |
| July 20 | Los Angeles Galaxy (MLS) | 3:2 | San Diego Flash (A-League) | |
| August 4 | DC United (MLS) | 3:4 (ASDET) | Charleston Battery (A-League) | |
| Quarterfinals | Away Team | Result | Home Team | |
| August 11 | Columbus Crew (MLS) | 3:1 | Los Angeles Galaxy (MLS) | |
| August 11 | Dallas Burn (MLS) | 1:2 (ASDET) | Rochester Raging Rhinos (A-League) | |
| August 13 | Colorado Rapids (MLS) | 1:0 | Tampa Bay Mutiny (MLS) | |
| August 18 | Staten Island Vipers (A-League) | 1:2 | Charleston Battery (A-League) | |
| Semifinals | Away Team | Result | Home Team | |
| September 1 | Rochester Raging Rhinos (A-League) | 3:2 | Columbus Crew (MLS) | |
| September 1 | Charleston Battery (A-League) | 0:3 | Colorado Rapids (MLS) | |
| Final (Columbus Crew Stadium – Columbus, Ohio) | ||||
| September 14 | Rochester Raging Rhinos (A-League) | 2:0 | Colorado Rapids (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) | ||||
