| First Round | Away Team | Result | Home Team | ||
| June 2 | Bavarian SC (USASA) | 1:5 | Carolina Dynamo (PDL) | ||
| June 2 | Allied SC (USASA) | 0:5 | South Jersey Barons (PDL) | ||
| June 2 | Chicago Fire Reserves (PDL) | 5:1 | SAC Wisla (USASA) | ||
| June 2 | Cape Cod Crusaders (PDL) | 4:1 | NY Greek American Atlas (USASA) | ||
| June 2 | Sacramento Knights (USASA) | 2:1 (ASDET) | Spokane Shadow (PDL) | ||
| June 2 | Boulder Rapids Reserve (PDL) | 2:1 | Chico Rooks (USASA) | ||
| June 8 | Legends FC (USASA) | 1:3 | DFW Tornadoes (PDL) | ||
| June 8 | Azzurri (USASA) | 2:3 (ASDET) | Cocoa Expos (PDL) | ||
| Second Round | Away Team | Result | Home Team | ||
| June 15 | San Diego Gauchos (PSL) | 0:0 (4:5 PKs) | Boulder Rapids Reserve (PDL) | ||
| June 15 | Sacramento Knights (USASA) | 0:3 | Utah Blitzz (PSL) | ||
| June 15 | DFW Tornadoes (PDL) | 0:2 | Virginia Beach Mariners (A-League) | ||
| June 15 | Chicago Fire Reserves (PDL) | 5:1 | New Hampshire Phantoms (PSL) | ||
| June 15 | Cape Cod Crusaders (PDL) | 3:2 | Western Mass Pioneers (PSL) | ||
| June 15 | Cocoa Expos (PDL) | 0:3 | Wilmington Hammerheads (PSL) | ||
| June 15 | Charlotte Eagles (PSL) | 2:4 | Carolina Dynamo (PDL) | ||
| June 21 | Syracuse Salty Dogs (A-League) | 4:2 | South Jersey Barons (PDL) | ||
| Third Round | Away Team | Result | Home Team | ||
| June 30 | Portland Timbers (A-League) | 2:1 | Utah Blitzz (PSL) | ||
| June 30 | Boulder Rapids Reserve (PDL) | 1:2 (ASDET) | Minnesota Thunder (A-League) | ||
| June 30 | Wilmington Hammerheads (PSL) | 0:2 | Charleston Battery (A-League) | ||
| June 30 | Atlanta Silverbacks (A-League) | 3:2 (ASDET) | Carolina Dynamo (PDL) | ||
| June 30 | Colorado Rapids (MLS) | 0:3 | Dallas Burn (MLS) | ||
| June 30 | Cape Cod Crusaders (PDL) | 0:1 (ASDET) | Richmond Kickers (A-League) | ||
| June 30 | Syracuse Salty Dogs (A-League) | 1:2 | Columbus Crew (MLS) | ||
| June 30 | Chicago Fire Reserves (PDL) | 0:1 | Rochester Raging Rhinos (A-Lg) | ||
| Fourth Round | Away Team | Result | Home Team | ||
| July 14 | San Jose Earthquakes (MLS) | 3:0 | Portland Timbers (A-League) | ||
| July 20 | Los Angeles Galaxy (MLS) | 0:1 | Minnesota Thunder (A-League) | ||
| July 20 | Colorado Rapids (MLS) | 0:3 | Dallas Burn (MLS) | ||
| July 20 | Rochester Raging Rhinos (A-Lg) | 1:1 (3:1 PKs) | New England Revolution (MLS) | ||
| July 20 | Chicago Fire (MLS) | 2:1 (ASDET) | Columbus Crew (MLS) | ||
| July 20 | Kansas City Wizards (MLS) | 4:1 | Atlanta Silverbacks (A-League) | ||
| July 20 | Metrostars (MLS) | 0:1 | Charleston Battery (A-League) | ||
| July 21 | DC United (MLS) | 1:2 | Richmond Kickers (A-League) | ||
| Quarterfinals | Away Team | Result | Home Team | ||
| August 4 | San Jose Earthquakes (MLS) | 2:2 (5:4 PKs) | Minnesota Thunder (A-League) | ||
| August 4 | Dallas Burn (MLS) | 0:4 | Kansas City Wizards (MLS) | ||
| August 4 | Chicago Fire (MLS) | 1:0 | Richmond Kickers (A-League) | ||
| August 4 | Charleston Battery (A-League) | 1:0 | Rochester Raging Rhinos (A-Lg) | ||
| Semifinals | Away Team | Result | Home Team | ||
| August 24 | San Jose Earthquakes (MLS) | 0:1 | Kansas City Wizards (MLS) | ||
| August 25 | Charleston Battery (A-League) | 0:1 (ASDET) | Chicago Fire (MLS) | ||
| Final (Arrowhead Stadium – Kansas City, Mo.) | |||||
| September 22 | Chicago Fire (MLS) | 0:1 (ASDET) | Kansas City Wizards (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) | |||||