| First Round | Away Team | Result | Home Team | |
| June 9 | San Nicholas (USASA) | 1:2 | Austin Lone Stars (D3 Pro) | |
| June 10 | Detroit Dynamite (PDSL) | 1:2 (ASDET) | Delaware Wizards (D3 Pro) | |
| June 11 | SAC Wisla (USASA) | 0:8 | Chicago Stingers (D3 Pro) | |
| June 12 | San Gabriel Valley Highlanders (PDSL) | 1:2 | Arizona Sahuaros (D3 Pro) | |
| June 12 | Los Lobos (USASA) | 3:4 | Charlotte Eagles (D3 Pro) | |
| June 13 | Kansas City Brass (PDSL) | 1:2 (ASDET) | Central Jersey Riptide (D3 Pro) | |
| June 16 | Jackson Chargers (PDSL) | 1:2 | Orlando Nighthawks (D3 Pro) | |
| June 21 | NY Greek American Atlas (USASA) | 0:2 (Forfeit) | Western Mass Pioneers (D3 Pro) | |
| Second Round | Away Team | Result | Home Team | |
| June 23 | Austin Lone Stars (D3 Pro) | 1:2 | Orange County Zodiac (A-League) | |
| June 23 | Orlando Nighthawks (D3 Pro) | 2:1 | Milwaukee Rampage (A-League) | |
| June 23 | Chicago Stingers (D3 Pro) | 3:2 (ASDET) | Hershey Wildcats (A-League) | |
| June 23 | Charlotte Eagles (D3 Pro) | 0:2 | Worcester Wildfire (A-League) | |
| June 24 | Arizona Sahuaros (D3 Pro) | 1:9 | El Paso Patriots (A-League) | |
| June 24 | Delaware Wizards (D3 Pro) | 1:7 | Nashville Metros (A-League) | |
| June 30 | Central Jersey Riptide (D3 Pro) | 0:0 (2:3 PKs) | Hampton Roads Mariners (A-Lg.) | |
| July 1 | Rochester Raging Rhinos (A-League) | 3:1 | Western Mass Pioneers (D3 Pro) | |
| Third Round | Away Team | Result | Home Team | |
| July 6 | Chicago Fire (MLS) | 3:1 | Chicago Stingers (D3 Pro) | |
| July 7 | San Jose Clash (MLS) | 2:0 | El Paso Patriots (A-League) | |
| July 7 | Columbus Crew (MLS) | 2:1 (ASDET) | Rochester Raging Rhinos (A-League) | |
| July 8 | Hampton Roads Mariners (A-Lg.) | 0:1 (ASDET) | Metrostars (MLS) | |
| July 8 | Worcester Wildfire (A-League) | 2:2 (4:5 PKs) | Tampa Bay Mutiny (MLS) | |
| July 8 | Orlando Nighthawks (D3 Pro) | 0:3 | Miami Fusion (MLS) | |
| July 8 | Orange County Zodiac (A-League) | 0:4 | Dallas Burn (MLS) | |
| July 8 | Kansas City Wizards (MLS) | 1:3 | Nashville Metros (A-League) | |
| Quarterfinals | Away Team | Result | Home Team | |
| July 22 | Miami Fusion (MLS) | 0:3 | Columbus Crew (MLS) | |
| July 22 | Tampa Bay Mutiny (MLS) | 0:4 | Metrostars (MLS) | |
| July 22 | San Jose Clash (MLS) | 1:1 (3:4 PKs) | Chicago Fire (MLS) | |
| July 22 | Nashville Metros (A-League) | 1:5 | Dallas Burn (MLS) | |
| Semifinals | Away Team | Result | Home Team | |
| August 4 | Metrostars (MLS) | 0:1 | Columbus Crew (MLS) | |
| August 4 | Dallas Burn (MLS) | 2:3 | Chicago Fire (MLS) | |
| Note: Both Semifinal matches played at Zephyr Field in Metairie, Louisiana | ||||
| Final (Soldier Field – Chicago, Ill.) | ||||
| October 30 | Columbus Crew (MLS) | 1:2 (ASDET) | 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 Soccer League (PDSL) | |||
| US Amateur Soccer Assoc. (USASA) | ||||