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| ROUND 1 | AWAY TEAM | TIME | HOME TEAM | VENUE | A/V |
| May 9 | South Florida Surf (PDL) | 4:2 | Red Force FC (USASA) | Tropical Park – Miami, FL | VIDEO |
| May 10 | Christos FC (USASA) | 3:0 | Fredericksburg FC (NPSL) | Univ. of Mary Washington Battleground Stadium – F’burg, VA | VIDEO |
| May 10 | SC United Bantams (PDL) | 1:4 | Atlanta Silverbacks (NPSL) | Atlanta Silverbacks Park – Atlanta, GA | VIDEO |
| May 10 | Burlingame Dragons (PDL) | 0:0 (6:5 PK) | El Farolito (USASA) | Boxer Stadium – San Francisco, CA | NONE |
| May 10 | Boston City FC (NPSL) | 2:2 (5:4 PK) | Western Mass Pioneers (PDL) | Lusitano Stadium – Ludlow, MA | VIDEO |
| May 10 | FC Motown (USASA) | 2:1 (AET) | New Jersey Copa FC (NPSL) | Saint John Vianney HS – Holmdel, NJ | VIDEO |
| May 10 | Chattanooga FC (NPSL) | 0:2 | Charlotte Eagles (PDL) | Charlotte Christian School – Charlotte, NC | VIDEO |
| May 10 | Legacy 76 (NPSL) | 1:2 | Carolina Dynamo (PDL) | Macpherson Stadium – Greensboro, NC | VIDEO |
| May 10 | Boca Raton FC (USASA) | 1:2 | Miami United (NPSL) | Ted Hendricks Stadium – Hialeah, FL | VIDEO |
| May 10 | The Villages SC (PDL) | 1:2 | Jacksonville Armada U23s (NPSL) | Patton Park – Jacksonville, FL | VIDEO |
| May 10 | Junior Lone Star FC (USASA) | 1:3 | Ocean City Nor’easters (PDL) | Carey Stadium – Ocean City, NJ | RADIO |
| May 10 | Clarkstown SC Eagles (NPSL) | 0:1 | Reading United AC (PDL) | Exeter High School Don Thomas Stadium – Reading, PA | VIDEO |
| May 10 | AFC Ann Arbor (NPSL) | 0:1 | Michigan Bucks (PDL) | Ultimate Soccer Arenas – Pontiac, MI | VIDEO |
| May 10 | Tartan Devils Oak Avalon (USASA) | 1:1 (5:4 PK) | Derby City Rovers (PDL) | Woehrle Athletic Complex – Jeffersonville, IN | NONE |
| May 10 | GPS Omens (USASA) | 2:0 | GPS Portland Phoenix (PDL) | Memorial Field – Portland, ME | NONE |
| May 10 | North Texas Rayados (USASA) | 1:3 | Dutch Lions FC (NPSL) | Dutch Lions FC Soccer Facility – Conroe, TX | VIDEO |
| May 10 | Azteca FC (USSSA) | 0:1 (AET) | FC Wichita (NPSL) | Stryker Soccer Complex – Wichita, KS | VIDEO |
| May 10 | AFC Cleveland (NPSL) | 3:1 | Des Moines Menace (PDL) | Valley Stadium – West Des Moines, IA | VIDEO |
| May 10 | Oklahoma City Energy U23s (PDL) | 1:1 (4:2 PK) | Tulsa Athletic (NPSL) | Hurricane Soccer & Track Stadium – Tulsa, OK | VIDEO |
| May 10 | Anahuac FC (USASA) | 1:1 (5:4 PK) | Sonoma County Sol (NPSL) | Casa Grande High School – Petaluma, CA | NONE |
| May 10 | Chula Vista FC (USASA) | 3:2 | Albion SC Pros (NPSL) | Mission Bay HS – San Diego, CA | VIDEO |
| May 10 | Outbreak FC (USASA) | 0:2 | FC Golden State Force (PDL) | Citrus College – Glendora, CA | NONE |
| May 10 | La Maquina (USASA) | 1:4 | Fresno Fuego (PDL) | Chukchansi Park – Fresno, CA | VIDEO |
| May 10 | Moreno Valley FC (USASA) | 2:1 | Ventura County Fusion (PDL) | Ventura County Sportsplex – Ventura, CA | VIDEO |
| May 10 | Colorado Rush (USSSA) | 1:3 | FC Tucson (PDL) | Kino North Stadium – Tucson, AZ | VIDEO |
| May 10 | Sounders FC U23s (PDL) | 0:0 (3:5 PK) | OSA FC (NPSL) | Seattle HS Memorial Stadium – Seattle, WA | VIDEO |
| May 10 | San Diego Zest (PDL) | 2:4 | LA Wolves FC (USASA) | Azusa Pacific University Field – Azusa, CA | VIDEO |
| May 12 | Grand Rapids FC (NPSL) | 0:1 | Chicago FC United (PDL) | Wheaton College – Wheaton, IL | VIDEO |
| ROUND 2 | AWAY TEAM | TIME | HOME TEAM | VENUE | A/V |
| May 16 | Jacksonville Armada U23s (NPSL) | 0:3 | Tampa Bay Rowdies (USL) | Al Lang Stadium – St. Petersburg, FL | VIDEO |
| May 17 | Charleston Battery (USL) | 2:1 | Atlanta Silverbacks (NPSL) | Atlanta Silverbacks Park – Atlanta, GA | VIDEO |
| May 17 | New York Cosmos (NASL) | 2:3 | Reading United AC (PDL) | Shirk Stadium – Reading, PA | VIDEO |
| May 17 | GPS Omens (USASA) | 2:1 | Boston City FC (NPSL) | Della Russo Stadium, Revere, MA | VIDEO |
| May 17 | Christos FC (USASA) | 1:0 | Richmond Kickers (USL) | City Stadium – Richmond, VA | VIDEO |
| May 17 | FC Motown (USASA) | 0:3 | Rochester Rhinos (USL) | Capelli Sport Stadium – Rochester, NY | VIDEO |
| May 17 | Jacksonville Armada (NASL) | 2:1 | Miami United (NPSL) | Ted Hendricks Stadium – Hialeah, FL | VIDEO |
| May 17 | North Carolina FC (NASL) | 6:1 | Carolina Dynamo (PDL) | Macpherson Stadium – Greensboro, NC | VIDEO |
| May 17 | Charlotte Independence (USL) | 3:2 | Charlotte Eagles (PDL) | Charlotte Christian School – Charlotte, NC | VIDEO |
| May 17 | Louisville City FC (USL) | 9:0 | Tartan Devils Oak Avalon (USASA) | Highmark Stadium – Pittsburgh, PA | NONE |
| May 17 | AFC Cleveland (NPSL) | 0:1 (AET) | FC Cincinnati (USL) | Nippert Stadium – Cincinnati, OH | NONE |
| May 17 | Indy Eleven (NASL) | 0:1 | Michigan Bucks (PDL) | Ultimate Soccer Arenas – Pontiac, MI | VIDEO |
| May 17 | South Florida Surf (PDL) | 2:3 | Miami FC (NASL) | Cobb Field (Univ. of Miami)- Coral Gables, FL | VIDEO |
| May 17 | Harrisburg City Islanders (USL) | 0:0 (6:5 PK) | Ocean City Nor’easters (PDL) | Carey Stadium – Ocean City, NJ | AUDIO |
| May 17 | Pittsburgh Riverhounds (USL) | 1:3 | Chicago FC United (PDL) | Hoyne Field (Loyola Univ.) – Chicago, IL | VIDEO |
| May 17 | Saint Louis FC (USL) | 4:3 (AET) | FC Wichita (NPSL) | Stryker Soccer Complex – Wichita, KS | VIDEO |
| May 17 | San Antonio FC (USL) | 2:1 | Dutch Lions FC (NPSL) | Dutch Lions FC Soccer Facility – Conroe, TX | VIDEO |
| May 17 | OKC Energy U23s (PDL) | 3:5 | Tulsa Roughnecks (USL) | Hurricane Soccer & Track Stadium – Tulsa, OK | VIDEO |
| May 17 | Moreno Valley FC (USASA) | 1:5 | Oklahoma City Energy FC (USL) | Taft Stadium – Oklahoma City, OK | VIDEO |
| May 17 | FC Tucson (PDL) | 0:2 | Colorado Springs Switchbacks FC (USL) | Weidner Field – Colorado Springs, CO | NONE |
| May 17 | Phoenix Rising (USL) | 3:1 | Fresno Fuego (PDL) | Fresno State Soccer & Lacrosse Stadium – Fresno, CA | VIDEO |
| May 17 | Orange County SC (USL) | 5:2 | FC Golden State Force (PDL) | Citrus College – Glendora, CA | NONE |
| May 17 | Chula Vista FC (USASA) | 0:1 (AET) | Los Angeles Wolves FC (USASA) | Azusa Pacific Univ. – Azusa, CA | NONE |
| May 17 | Anahuac FC (USASA) | 0:4 | Sacramento Republic FC (USL) | Papa Murphy’s Park – Sacramento, CA | VIDEO |
| May 17 | Burlingame Dragons (PDL) | 1:2 | San Francisco Deltas (NASL) | Stanford University – Stanford, CA | VIDEO |
| May 17 | Reno 1868 FC (USL) | 1:1 (4:3 PK) | OSA FC (NPSL) | Starfire Sports Complex – Tukwila, WA | VIDEO |
| ROUND 3 | AWAY TEAM | TIME | HOME TEAM | VENUE | A/V |
| May 30 | Saint Louis FC (USL) | 2:1 | Michigan Bucks (PDL) | Ultimate Soccer Arenas – Pontiac, MI | VIDEO |
| May 31 | GPS Omens (USASA) | 1:2 (AET) | Rochester Rhinos (USL) | Capelli Sport Stadium – Rochester, NY | VIDEO |
| May 31 | Charleston Battery (USL) | 1:0 | Jacksonville Armada (NASL) | Southern Oak Stadium (Jacksonville Univ.) – Jacksonville, FL | VIDEO |
| May 31 | Louisville City FC (USL) | 0:1 | FC Cincinnati (USL) | Nippert Stadium (Univ. of Cincinnati) – Cincinnati, OH | VIDEO |
| May 31 | Harrisburg City Islanders (USL) | 3:0 | Reading United AC (PDL) | Exeter Township Senior HS – Reading, PA | VIDEO |
| May 31 | Charlotte Independence (USL) | 1:4 | North Carolina FC (NASL) | Sahlen’s Stadium at WakeMed Park – Cary, NC | VIDEO |
| May 31 | Tampa Bay Rowdies (USL) | 0:2 | Miami FC (NASL) | FIU Stadium – Miami, FL | ESPN3 |
| May 31 | Christos FC (USASA) | 1:0 | Chicago FC United (PDL) | Hoyne Field (Loyola Univ.) – Chicago, IL | VIDEO |
| May 31 | San Antonio FC (USL) | 0:0 (6:7 PK) | Tulsa Roughnecks (USL) | Hurricane Soccer & Track Stadium | VIDEO |
| May 31 | Oklahoma City Energy FC (USL) | 2:1 | Colorado Springs Switchbacks FC (USL) | Weidner Field – Colorado Springs, CO | VIDEO |
| May 31 | San Francisco Deltas (NASL) | 2:1 | Phoenix Rising (USL) | Phoenix Rising Soccer Complex – Scottsdale, AZ | VIDEO |
| May 31 | Orange County SC (USL) | 1:0 | Los Angeles Wolves (USASA) | Azusa Pacific University – Azusa, CA | VIDEO |
| May 31 | Reno 1868 FC (USL) | 0:2 | Sacramento Republic (USL) | Papa Murphy’s Park – Sacramento, CA |
VIDEO |
| ROUND 4 | AWAY TEAM | SCORE | HOME TEAM | VENUE | A/V |
| June 13 | Christos FC (USASA) | 1:4 | D.C. United (MLS) | Maryland Soccerplex – Boyds, MD | VIDEO |
| June 13 | Oklahoma City Energy FC (USL) | 2:3 | Colorado Rapids (MLS) | Dick’s Sporting Goods Park – Commerce City, CO | VIDEO |
| June 13 | Portland Timbers (MLS) | 1:2 | Seattle Sounders FC (MLS) | Starfire Sports Complex – Tukwila, WA | VIDEO |
| June 14 | Columbus Crew (MLS) | 0:1 | FC Cincinnati (USL) | Nippert Stadium (Univ. of Cincinnati) – Cincinnati, OH | VIDEO |
| June 14 | Houston Dynamo (MLS) | 3:2 (AET) | North Carolina FC (NASL) | Sahlen’s Stadium at WakeMed Park – Cary, NC | VIDEO |
| June 14 | Rochester Rhinos (USL) | 0:3 | New England Revolution (MLS) | Anderson Stadium (Providence College) – Providence, RI | VIDEO |
| June 14 | Harrisburg City Islanders (USL) | 1:3 | Philadelphia Union (MLS) | Talen Energy Stadium – Chester, PA | VIDEO |
| June 14 | Charleston Battery (USL) | 2:3 | Atlanta United (MLS) | Fifth Third Bank Stadium (Kennesaw State Univ.) – Kennesaw, GA | VIDEO |
| June 14 | Miami FC (NASL) | 3:1 | Orlando City SC (MLS) | Orlando City Stadium – Orlando, FL | VIDEO |
| June 14 | New York City FC (MLS) | 0:1 | New York Red Bulls (MLS) | Red Bull Arena – Harrison, NJ | VIDEO |
| June 14 | Chicago Fire (MLS) | 1:0 | Saint Louis FC (USL) | Toyota Stadium (WWT Soccer Park) – Fenton, MO | VIDEO |
| June 14 | Tulsa Roughnecks (USL) | 1:2 | FC Dallas (MLS) | Westcott Field (SMU) – Dallas, TX | VIDEO |
| June 14 | Minnesota United FC (MLS) | 0:4 | Sporting Kansas City (MLS) | Children’s Mercy Park – Kansas City, KS | VIDEO |
| June 14 | Orange County SC (USL) | 1:3 | Los Angeles Galaxy (MLS) | StubHub Center Track Stadium – Carson, CA | VIDEO |
| June 14 | San Francisco Deltas (NASL) | 0:2 | San Jose Earthquakes (MLS) | Avaya Stadium – San Jose, CA | VIDEO |
| June 14 | Real Salt Lake (MLS) | 1:4 | Sacramento Republic (USL) | Papa Murphy’s Park – Sacramento, CA | VIDEO |
| ROUND 5 (Rd of 16) | AWAY TEAM | SCORE | HOME TEAM | A/V | |
| June 27 | Colorado Rapids (MLS) | 1:3 | FC Dallas (MLS) | Toyota Stadium – Frisco, TX | VIDEO |
| June 28 | Sporting Kansas City (MLS) | 2:0 | Houston Dynamo (MLS) | BBVA Compass Stadium – Houston, TX | VIDEO |
| June 28 | D.C. United (MLS) | 1:2 | New England Revolution (MLS) | Jordan Field (Harvard Univ.) – Boston, MA | VIDEO |
| June 28 | Atlanta United (MLS) | 2:3 | Miami FC (NASL) | Riccardo Silva Stadium (Florida Int’l Univ) – Miami, FL | VIDEO |
| June 28 | Chicago Fire (MLS) | 0:0 (1:3 PK) | FC Cincinnati (USL) | Nippert Stadium – Cincinnati, OH | ESPN |
| June 28 | Philadelphia Union (MLS) | 1:1 (3:5 PK) | New York Red Bulls (MLS) | Red Bull Arena – Harrison, NJ | VIDEO |
| June 28 | Seattle Sounders FC (MLS) | 1:2 | San Jose Earthquakes (MLS) | Avaya Stadium – San Jose, CA | VIDEO |
| June 28 | Sacramento Republic (USL) | 0:2 | Los Angeles Galaxy (MLS) | StubHub Center Track Stadium – Carson, CA | VIDEO |
| Q-FINALS | AWAY TEAM | SCORE | HOME TEAM | A/V | |
| July 10 | Los Angeles Galaxy (MLS) | 2:3 | San Jose Earthquakes (MLS) | Avaya Stadium – San Jose, CA | VIDEO |
| July 11 | FC Dallas (MLS) | 0:3 (AET) | Sporting Kansas City (MLS) | Children’s Mercy Park – Kansas City, KS | VIDEO |
| July 13 | New York Red Bulls (MLS) | 1:0 | New England Revolution (MLS) | Jordan Field (Harvard Univ.) – Boston, MA | VIDEO |
| Aug. 2 | FC Cincinnati (USL) | 1:0 | Miami FC (NASL) | Riccardo Silva Stadium (Florida International Univ.) – Miami, FL | VIDEO |
| SEMIFINALS | AWAY TEAM | SCORE | HOME TEAM | A/V | |
| Aug. 9 | San Jose Earthquakes (MLS) | 1:1 (4:5 PKs) | Sporting Kansas City (MLS) | Children’s Mercy Park – Kansas City, KS | VIDEO |
| Aug. 15 | New York Red Bulls (MLS) | 3:2 (AET) | FC Cincinnati (USL) | Nippert Stadium (Univ. of Cincinnati) – Cincinnati, OH | VIDEO |
| FINAL | AWAY TEAM | SCORE | HOME TEAM | A/V | |
| Sept. 20 | New York Red Bulls (MLS) | 1:2 | Sporting Kansas City (MLS) | Children’s Mercy Park – Kansas City, KS | ESPN2 |