| First Round | Away Team | Result | Home Team |
| June 18 | Tucson Amigos (PDSL) | 2:4 | Austin Lone Stars (D3 Pro) |
| June 20 | Albuquerque Geckos (D3 Pro) | 2:4 | Central Coast Roadrunners (PDSL) |
| June 20 | San Francisco Bay Seals (D3 Pro) | 4:0 | Inter SC (USASA) |
| June 24 | Mid-Michigan Bucks (PDSL) | 3:2 | Wilmington Hammerheads (D3 Pro) |
| June 24 | Mequon United (USASA) | 0:2 | Chicago Stingers (D3 Pro) |
| June 25 | Lincoln Brigade (PDSL) | 1:1 (4:5 PKs) | Philadelphia Freedom (D3 Pro) |
| June 25 | Central Jersey Riptide (D3 Pro) | 1:0 | Los Lobos (USASA) |
| June 26 | Bridgeport Italians (USASA) | 3:2 | Rhode Island Stingrays (D3 Pro) |
| Second Round | Away Team | Result | Home Team |
| July 1 | New Orleans Riverboat Gamblers (A-Lg.) | 1:0 (ASDET) | Austin Lone Stars (D3 Pro) |
| July 2 | Philadelphia Freedom (D3 Pro) | 1:6 | Richmond Kickers (A-League) |
| July 7 | California Jaguars (A-League) | 2:3 (ASDET) | Central Coast Roadrunners (PDSL) |
| July 8 | Mid-Michigan Bucks (PDSL) | 2:3 (ASDET) | Rochester Raging Rhinos (A-Lg.) |
| July 8 | Central Jersey Riptide (D3 Pro) | 1:4 | Hershey Wildcats (A-League) |
| July 8 | Orlando Sundogs (A-League) | 0:3 | Chicago Stingers (D3 Pro) |
| July 8 | Seattle Sounders (A-League) | 0:1 | San Francisco Bay Seals (D3 Pro) |
| July 13 | Bridgeport Italians (USASA) | 0:1 | Long Island Rough Riders (A-League) |
| Third Round | Away Team | Result | Home Team |
| July 23 | Metrostars (MLS) | 3:0 | Richmond Kickers (A-League) |
| July 24 | Kansas City Wizards (MLS) | 1:2 | San Francisco Bay Seals (D3 Pro) |
| July 27 | San Jose Clash (MLS) | 5:2 | Central Coast Roadrunners (PDL) |
| July 29 | Dallas Burn (MLS) | 3:0 | New Orleans Riverboat Gamblers (A-Lg.) |
| July 30 | Colorado Rapids (MLS) | 1:2 | Chicago Stingers (D3 Pro) |
| August 1 | Long Island Rough Riders (A-League) | 4:3 (ASDET) | New England Revolution (MLS) |
| August 1 | Tampa Bay Mutiny (MLS) | 1:0 | Rochester Raging Rhinos (A-League) |
| August 6 | DC United (MLS) | 0:0 (3:2 PKs) | Hershey Wildcats (A-League) |
| Quarterfinals | Away Team | Result | Home Team |
| August 10 | Dallas Burn (MLS) | 4:1 | Chicago Stingers (D3 Pro) |
| August 19 | Tampa Bay Mutiny (MLS) | 0:2 | DC United (MLS) |
| August 20 | San Francisco Bay Seals (D3 Pro) | 2:1 | San Jose Clash (MLS) |
| August 26 | Metrostars (MLS) | 1:0 (ASDET) | Long Island Rough Riders (A-League) |
| Semifinals | Away Team | Result | Home Team |
| September 2 | Dallas Burn (MLS) | 2:1 (ASDET) | Metrostars (MLS) |
| September 3 | San Francisco Bay Seals (D3 Pro) | 1:2 | DC United (MLS) |
| Final (Track & Field Stadium at IUPUI – Indianapolis, Ind.) | |||
| October 29 | DC United (MLS) | 0:0 (3:5 PKs) | Dallas Burn (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 Soccer League (PDL) | ||
| US Amateur Soccer Assoc. (USASA) | |||
