| First Round | Away Team | Result | Home Team | |
| June 4 | Mexico SC (USASA) | 3:2 | San Gabriel Valley Highlanders (PDL) | |
| June 5 | Uruguay SC (USASA) | 2:1 | Central Florida Kraze (PDL) | |
| June 6 | Bavarian SC (USASA) | 0:3 | Chicago Sockers (PDL) | |
| June 6 | Jerry D’s (USASA) | 0:6 | Mid-Michigan Bucks (PDL) | |
| Second Round | Away Team | Result | Home Team | |
| June 13 | San Diego Flash (A-League) | 2:1 | Riverside County Elite (D3 Pro) | |
| June 14 | Seattle Sounders (A-League) | 1:2 | Los Angeles Galaxy (MLS) | |
| June 14 | Colorado Rapids (MLS) | 0:3 | Richmond Kickers (A-League) | |
| June 14 | San Jose Earthquakes (MLS) | 5:0 | Stanislaus United Cruisers (D3 Pro) | |
| June 14 | Texas Rattlers (D3 Pro) | 0:4 | Chicago Fire (MLS) | |
| June 14 | Kansas City Wizards (MLS) | 0:0 (6:7 PKs) | Chicago Sockers (PDL) | |
| June 14 | Tennessee Rhythm (A-League) | 0:3 | Dallas Burn (MLS) | |
| June 14 | Mexico SC (USASA) | 0:7 | Minnesota Thunder (A-League) | |
| June 14 | DC United (MLS) | 4:0 | Charleston Battery (A-League) | |
| June 14 | Rochester Raging Rhinos (A-Lg.) | 2:1 | Pittsburgh Riverhounds (A-League) | |
| June 14 | New Jersey Stallions (D3 Pro) | 1:6 | Miami Fusion (MLS) | |
| June 14 | Mid-Michigan Bucks (PDL) | 1:0 | New England Revolution (MLS) | |
| June 14 | Uruguay SC (USASA) | 0:1 (ASDET) | Tampa Bay Mutiny (MLS) | |
| June 14 | Metrostars (MLS) | 2:1 | Wilmington Hammerheads (D3 Pro) | |
| June 14 | Columbus Crew (MLS) | 2:0 | Cape Cod Crusaders (D3 Pro) | |
| June 14 | Northern Virginia Royals (D3 Pro) | 2:3 | Hampton Roads Mariners (A-League) | |
| Third Round | Away Team | Result | Home Team | |
| July 19 | Hampton Roads Mariners (A-Lg.) | 1:4 | Columbus Crew (MLS) | |
| July 25 | Los Angeles Galaxy (MLS) | 2:0 | San Diego Flash (A-League) | |
| July 25 | Richmond Kickers (A-League) | 0:2 | San Jose Earthquakes (MLS) | |
| July 25 | Chicago Fire (MLS) | 1:0 | Chicago Sockers (PDL) | |
| July 25 | Dallas Burn (MLS) | 2:0 | Minnesota Thunder (A-League) | |
| July 25 | Miami Fusion (MLS) | 3:3 (6:5 PKs) | Mid-Michigan Bucks (PDL) | |
| July 25 | Tampa Bay Mutiny (MLS) | 0:3 | Metrostars (MLS) | |
| July 26 | Rochester Raging Rhinos (A-Lg.) | 0:3 | DC United (MLS) | |
| Quarterfinals | Away Team | Result | Home Team | |
| August 9 | San Jose Earthquakes (MLS) | 0:2 | Los Angeles Galaxy (MLS) | |
| August 9 | Dallas Burn (MLS) | 1:5 | Chicago Fire (MLS) | |
| August 9 | Miami Fusion (MLS) | 3:2 (ASDET) | DC United (MLS) | |
| August 9 | Metrostars (MLS) | 1:1 (7:6 PKs) | Columbus Crew (MLS) | |
| Semifinals | Away Team | Result | Home Team | |
| August 23 | Chicago Fire (MLS) | 2:1 (ASDET) | Los Angeles Galaxy (MLS) | |
| September 12 | Miami Fusion (MLS) | 3:2 | Metrostars (MLS) | |
| Final (Soldier Field – Chicago, Ill.) | ||||
| October 21 | Miami Fusion (MLS) | 1:2 | Chicago Fire (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) | ||||
