| Qualifying Rd | Away Team | Result | Home Team | ||
| June 7 | Cape Cod Crusaders (PDL) | 2:0 | Allied SC (USASA) | ||
| June 7 | Croatian Eagles (USASA) | 1:4 | Des Moines Menace (PDL) | ||
| First Round | Away Team | Result | Home Team | ||
| June 14 | Pittsburgh Riverhounds (USL-2) | 0:2 | Michigan Bucks (PDL) | ||
| June 14 | Virginia Beach Submariners (PDL) | 1:3 | Wilmington Hammerheads (USL-2) | ||
| June 14 | Dallas Roma FC (USASA) | 2:2 (4:2 PKs) | Laredo Heat (PDL) | ||
| June 14 | Milford International (USASA) | 1:0 | Chicago Lightning (USASA) | ||
| June 14 | Dallas Mustang Legends (USASA) | 2:3 | Des Moines Menace (PDL) | ||
| June 14 | BYU Cougars (PDL) | 1:5 | Arizona Sahuaros (USASA) | ||
| June 14 | Ogden Outlaws (PDL) | 1:1 (5:6 PKs) | Sonoma County Sol (USASA) | ||
| June 15 | Cape Cod Crusaders (PDL) | 3:4 | Carolina Dynamo (PDL) | ||
| Second Round | Away Team | Result | Home Team | ||
| June 28 | Sonoma County Sol (USASA) | 0:1 | Charleston Battery (USL-1) | ||
| June 28 | Charlotte Eagles (USL-2) | 1:3 | Wilmington Hammerheads (USL-2) | ||
| June 28 | Virginia Beach Mariners (USL-1) | 1:0 | Arizona Sahuaros (USASA) | ||
| June 28 | Des Moines Menace (PDL) | 1:0 | Minnesota Thunder (USL-1) | ||
| June 28 | Cincinnati Kings (USL-2) | 1:2 | Michigan Bucks (PDL) | ||
| June 28 | Miami FC (USL-1) | 0:1 | Dallas Roma FC (USASA) | ||
| June 28 | Richmond Kickers (USL-2) | 0:1 | Carolina Dynamo (PDL) | ||
| June 28 | Milford International (USASA) | 1:4 | New Hampshire Phantoms (USL-2) | ||
| Third Round | Away Team | Result | Home Team | ||
| July 11 | Virginia Beach Mariners (USL-1) | 1:2 (AET) | Real Salt Lake (MLS) | ||
| July 12 | Portland Timbers (USL-1) | 1:3 | Charleston Battery (USL-1) | ||
| July 12 | Atlanta Silverbacks (USL-1) | 1:2 | Wilmington Hammerheads (USL-2) | ||
| July 12 | Des Moines Menace (PDL) | 1:2 | Kansas City Wizards (MLS) | ||
| July 12 | Columbus Crew (MLS) | 4:1 | Michigan Bucks (PDL) | ||
| July 12 | Dallas Roma FC (USASA) | 0:0 (4:2 PKs) | Chivas USA (MLS) | ||
| July 12 | Seattle Sounders (USL-1) | 2:3 (AET) | Carolina Dynamo (PDL) | ||
| July 12 | New Hampshire Phantoms (USL-2) | 1:5 | Rochester Raging Rhinos (USL-1) | ||
| Fourth Round | Away Team | Result | Home Team | ||
| August 1 | Dallas Roma FC (USASA) | 0:2 | Los Angeles Galaxy (MLS) | ||
| August 1 | Columbus Crew (MLS) | 1:2 (AET) | DC United (MLS) | ||
| August 2 | New England Revolution (MLS) | 0:0 (5:4 PKs) | Rochester Raging Rhinos (USL-1) | ||
| August 2 | Colorado Rapids (MLS) | 1:0 | Real Salt Lake (MLS) | ||
| August 2 | FC Dallas (MLS) | 3:3 (5:3 PKs) | Charleston Battery (USL-1) | ||
| August 2 | Carolina Dynamo (PDL) | 2:4 | Houston Dynamo (MLS) | ||
| August 2 | New York Red Bulls (MLS) | 2:1 | Wilmington Hammerheads (USL-2) | ||
| August 14 | Kansas City Wizards (MLS) | 0:2 | Chicago Fire (MLS) | ||
| Quarterfinals | Away Team | Result | Home Team | ||
| August 23 | Colorado Rapids (MLS) | 1:3 (AET) | Los Angeles Galaxy (MLS) | ||
| August 23 | FC Dallas (MLS) | 0:3 | Houston Dynamo (MLS) | ||
| August 23 | New York Red Bulls (MLS) | 1:3 | DC United (MLS) | ||
| August 23 | New England Revolution (MLS) | 1:2 | Chicago Fire (MLS) | ||
| Semifinals | Away Team | Result | Home Team | ||
| September 6 | Houston Dynamo (MLS) | 1:3 | Los Angeles Galaxy (MLS) | ||
| September 6 | DC United (MLS) | 1:2 | Chicago Fire (MLS) | ||
| Final (Toyota Park – Bridgeview, Ill.) | |||||
| September 27 | Los Angeles Galaxy (MLS) | 1:3 | Chicago Fire (MLS) | ||
| Division 1: Major League Soccer (MLS) | AET | After Extra Time | |||
| Division 2: USL First Division (USL-1) | PKs | Penalty Kicks | |||
| Division 3: USL Second Division (USL-2) | |||||
| Division 4: Premier Development League (PDL) | |||||
| US Adult Soccer Assoc. (USASA) | |||||