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| FIRST ROUND | AWAY TEAM | SCORE | HOME TEAM |
| May 7 | Lehigh Valley United (NPSL) | 1:0 (AET) | GPS Portland Phoenix (PDL) |
| May 7 | RWB Adria (USASA) | 2:2 (3:1 PK) | Detroit City FC (NPSL) |
| May 7 | GPS Massachusetts (USASA) | 1:4 | Western Mass Pioneers (PDL) |
| May 7 | Vermont Voltage (PDL) | 1:2 | NY Red Bulls U23s (NPSL) |
| May 7 | Red Force FC (USASA) | 2:1 | Colorado Rovers (USSSA) |
| May 7 | CD Aguiluchos USA (NPSL) | 1:2 | Ventura County Fusion (PDL) |
| May 7 | SC Corinthians USA (USCS) | forfeit to | San Diego Flash (NPSL) |
| May 7 | Los Angeles Misioneros (PDL) | 1:1 (2:3 PK) | PSA Elite (USASA) |
| SECOND ROUND | AWAY TEAM | TIME | HOME TEAM |
| May 13 | Arizona United SC (USL PRO) | 3:2 | Portland Timbers U23s (PDL) |
| May 14 | Jacksonville United FC (NPSL) | 1:2 | Orlando City U23s (PDL) |
| May 14 | Dayton Dutch Lions (USL PRO) | 2:0 | Schwaben AC (USASA) |
| May 14 | Icon FC (USASA) | 1:4 | Baltimore Bohemians (PDL) |
| May 14 | New York Red Bulls U23s (NPSL) | 1:3 | P’burgh Riverhounds (USL PRO) |
| May 14 | NY Greek American Atlas (USASA) | 2:0 | Ocean City Nor’easters (PDL) |
| May 14 | Greater Binghamton FC (NPSL) | 2:5 | Reading United AC (PDL) |
| May 14 | Richmond Kickers (USL PRO) | 6:1 | RVA FC (NPSL) |
| May 14 | H’burg City Islanders (USL PRO) | 4:0 | Lehigh Valley United (NPSL) |
| May 14 | Carolina Dynamo (PDL) | 1:3 | Charlotte Eagles (USL PRO) |
| May 14 | RWB Adria (USASA) | 1:0 (AET) | Michigan Bucks (PDL) |
| May 14 | Ocala Stampede (PDL) | 1:4 | Orlando City (USL PRO) |
| May 14 | Panama City Beach Pirates (PDL) | 0:4 | Charleston Battery (USL PRO) |
| May 14 | Wilm. Hammerheads (USL PRO) | 1:3 | Chattanooga FC (NPSL) |
| May 14 | Western Mass Pioneers (PDL) | 1:2 (AET) | Rochester Rhinos (USL PRO) |
| May 14 | Brooklyn Italians SC (NPSL) | 4:2 | Jersey Express (PDL) |
| May 14 | Oklahoma City Energy (USL PRO) | 2:0 | Tulsa Athletics (NPSL) |
| May 14 | Real Colorado Foxes (PDL) | 0:3 | Des Moines Menace (USASA) |
| May 14 | NTX Rayados (USASA) | 4:4 (4:2 PK) | Austin Aztex (PDL) |
| May 14 | Orange County Blues (USL PRO) | 0:2 | Fresno Fuego (PDL) |
| May 14 | Red Force (USASA) | 1:2 | Laredo Heat (PDL) |
| May 14 | PSA Elite (USASA) | W:L (FOR) | San Diego Flash (NPSL) |
| May 14 | Ventura County Fusion (PDL) | 1:2 | Sacramento Republic (USL PRO) |
| May 14 | Cal FC (USASA) | 1:6 | LA Galaxy II (USL PRO) |
| THIRD ROUND | AWAY TEAM | TIME | HOME TEAM |
| May 27 | Reading United (PDL) | 1:2 (AET) | Rochester Rhinos (USL PRO) |
| May 28 | H’burg City Islanders (USL PRO) | 4:2 | Baltimore Bohemians (PDL) |
| May 28 | NY Greek American Atlas (USASA) | 1:2 | Richmond Kickers (USL PRO) |
| May 28 | RWB Adria (USASA) | 2:3 (AET) | P’gh Riverhounds (USL PRO) |
| May 28 | Charlotte Eagles (USL PRO) | 0:2 | Carolina RailHawks (NASL) |
| May 28 | Atlanta Silverbacks (NASL) | 5:0 | Chattanooga FC (NPSL) |
| May 28 | Orlando City U23s (PDL) | 2:2 (12:11 PK) | Charleston Battery (USL PRO) |
| May 28 | Tampa Bay Rowdies (NASL) | 1:4 | Orlando City SC (USL PRO) |
| May 28 | Brooklyn Italians (NPSL) | 0:2 | New York Cosmos (NASL) |
| May 28 | Dayton Dutch Lions (USL PRO) | 2:5 | Indy Eleven (NASL) |
| May 28 | Laredo Heat (PDL) | 3:2 | Ft Lauderdale Strikers (NASL) |
| May 28 | NTX Rayados (USASA) | 2:4 | San Antonio Scorpions (NASL) |
| May 28 | Minnesota United FC (NASL) | 1:0 | Des Moines Menace (USASA) |
| May 28 | OKC Energy FC (USL PRO) | 1:2 (AET) | Arizona United SC (USL PRO) |
| May 28 | Fresno Fuego (PDL) | 0:6 | Sacramento Republic (USL PRO) |
| May 28 | PSA Elite (USASA) | 0:0 (3:1 PK) | LA Galaxy II (USL PRO) |
| FOURTH ROUND | AWAY TEAM | SCORE | HOME TEAM |
| June 11 | Laredo Heat (PDL) | 0:1 | Houston Dynamo (MLS) |
| June 11 | Sacramento Republic (USL PRO) | 1:2 | San Jose Earthquakes (MLS) |
| June 14 | Real Salt Lake (MLS) | 1:2 | Atlanta Silverbacks (NASL) |
| June 14 | Chivas USA (MLS) | 1:1 (2:3 PK) | Carolina RailHawks (NASL) |
| June 14 | New York Red Bulls (MLS) | 0:3 | New York Cosmos (NASL) |
| June 17 | DC United (MLS) | 0:1 | Rochester Rhinos (USL PRO) |
| June 17 | H’burg City Islanders (USL PRO) | 1:3 (AET) | Philadelphia Union (MLS) |
| June 17 | Indy Eleven (NASL) | 1:2 (AET) | Columbus Crew (MLS) |
| June 17 | San Antonio Scorpions (NASL) | 0:2 | FC Dallas (MLS) |
| June 17 | Orlando City SC (USL PRO) | 2:5 | Colorado Rapids (MLS) |
| June 17 | Orlando City U23s (PDL) | 0:3 | Portland Timbers FC (MLS) |
| June 18 | New England Revolution (MLS) | 3:2 | Richmond Kickers (USL PRO) |
| June 18 | P’burgh Riverhounds (USL PRO) | 1:2 (49′)* | Chicago Fire (MLS) |
| June 18 | Minnesota United FC (NASL) | 0:2 | Sporting Kansas City (MLS) |
| June 18 | PSA Elite (USASA) | 0:5 | Seattle Sounders FC (MLS) |
| June 18 | Los Angeles Galaxy (MLS) | 2:1 | Arizona United SC (USL PRO) |
| *Officials ended match in 49th minute due to inclement weather, Chicago wins | |||
| FIFTH ROUND | AWAY TEAM | SCORE | HOME TEAM |
| June 24 | New York Cosmos (NASL) | 1:2 (AET) | Philadelphia Union (MLS) |
| June 24 | LA Galaxy (MLS) | 0:1 (AET) | Carolina RailHawks (NASL) |
| June 24 | Portland Timbers FC (MLS) | 3:1 | Sporting KC (MLS) |
| June 24 | Atlanta Silverbacks (NASL) | 2:1 | Colorado Rapids (MLS) |
| June 24 | FC Dallas (MLS) | 3:2 (AET) | Houston Dynamo (MLS) |
| June 24 | San Jose Earthquakes (MLS) | 1:1 (1:4 PK) | Seattle Sounders FC (MLS) |
| June 25 | Rochester Rhinos (USL PRO) | 1:2 | New England Revolution (MLS) |
| June 25 | Columbus Crew (MLS) | 2:4 (AET) |
Chicago Fire (MLS) |
| QUARTERFINALS | AWAY TEAM | SCORE | HOME TEAM |
| July 8 | New England Revolution (MLS) | 0:2 | Philadelphia Union (MLS) |
| July 9 | FC Dallas (MLS) | 5:2 | Carolina RailHawks (NASL) |
| July 9 | Chicago Fire (MLS) | 3:1 | Atlanta Silverbacks (NASL) |
| July 9 | Portland Timbers FC (MLS) | 1:3 (AET) | Seattle Sounders FC (MLS) |
| SEMIFINALS | AWAY TEAM | SCORE | HOME TEAM |
| August 12 | Philadelphia Union (MLS) | 1:1 (4:3 PK) | FC Dallas (MLS) |
| August 13 | Chicago Fire (MLS) | 0:6 | Seattle Sounders FC (MLS) |
| FINAL | AWAY TEAM | SCORE | HOME TEAM |
| September 16 | Seattle Sounders FC (MLS) | 3:1 (AET) | Philadelphia Union (MLS) |