First Round
| No. | Date | Match | Venue | |
| 1 | June |
Brooklyn Italians (NPSL) 1, N.Y. Pancyprian Freedoms (USASA) 2 | Belson Stadium, St. Johns University; Queens, N.Y. | |
| 2 | June 14 |
Western Mass. Pioneers (PDL) 0, FC New York (USL PRO) 3 | The Met Oval; Queens, N.Y. | |
| 3 | June 14 |
Reading United A.C. (PDL) 1, Harrisburg City Islanders (USL PRO) 2 | Skyline Sports Complex; Harrisburg, Pa. | |
| 4 | June 14 |
Phoenix SC (USASA-Pa.) 1, Rochester Rhinos (USL PRO) 2 | Sahlen's Stadium; Rochester, N.Y. | |
| 5 | June 14 |
Chattanooga FC (NPSL) 2 Pittsburgh Riverhounds (USL PRO) 3 (OT) | Chartiers Valley Stadium; Bridgeville, Pa. | |
| 6 | June 14 |
Dayton Dutch Lions (USL PRO) 1, Richmond Kickers (USL PRO) 4 | Richmond City Stadium; Richmond, Va. | |
| 7 | June 14 |
Charlotte Eagles (USL PRO) 3, Carolina Dynamo (PDL) 1 | Macpherson Stadium; Browns Summit, N.C. | |
| 8 | June 14 |
Central Florida Kraze (PDL) 0, Wilmington Hammerheads (USL PRO) 4 | Legion Stadium; Wilmington, N.C. | |
| 9 | June 14 |
ASC New Stars (USASA-Texas) 0, Orlando City Soccer Club (USL PRO) 4 | University of Central Florida Soccer Complex; Oviedo, Fla.* | |
| 10 | June 14 |
Regals FC (USASA-Texas) 0, Charleston Battery (USL PRO) 2 | Blackbaud Stadium; Charleston, S.C. | |
| 11 | June 14 |
AAC Eagles (USASA-Ill.) 0, Madison 56ers (NPSL) 4 | Breese Stevens Field; Madison, Wis. | |
| 12 | June 14 |
Chicago Fire PDL (PDL) 1, Iowa Menace (USASA) 0 | Valley Stadium; West Des Moines, Iowa | |
| 13 | June 14 |
DV8 Defenders (USASA-Calif.) 0, Real Colorado Foxes (PDL) 5 | Shea Stadium; Highlands Ranch, Colo. | |
| 14 | June 14 |
Kitsap Pumas (PDL) 0, Chivas El Paso Patriots (PDL) 0 Kitsap Pumas wins in PKs 6-5 |
Patriots Stadium; El Paso, Texas | |
| 15 | June 14 |
Hollywood United (NPSL) 1, Los Angeles Blues (USL PRO) 3 | Riverside Community College; Riverside, Calif. | |
| 16 | June 14 |
Doxa Italia (USASA-Calif.) 1, Ventura County Fusion (PDL) 3 | Ventura College; Ventura, Calif. |
Second Round
| No. | Date | Match | Venue | |
| 17 | June 21 |
FC New York (USL PRO) 0, N.Y. Pancyprian Freedoms (USASA) 0 FC New York wins in PKs 6-5 |
Belson Stadium, St. Johns University; Queens, N.Y. | |
| 18 | June 21 |
Rochester Rhinos (USL PRO) 1, Harrisburg City Islanders (USL PRO) 0 | Skyline Sports Complex; Harrisburg, Pa. | |
| 19 | June 21 |
Pittsburgh Riverhounds (USL PRO) 1, Richmond Kickers (USL PRO) 4 | Richmond City Stadium; Richmond, Va. | |
| 20 | June 21 |
Charlotte Eagles (USL PRO) 2, Wilmington Hammerheads (USL PRO) 3 | Legion Stadium; Wilmington, N.C. | |
| 21 | June 21 |
Orlando City Soccer Club (USL PRO) 1, Charleston Battery (USL PRO) 0 | Blackbaud Stadium; Charleston, N.C. | |
| 22 | June 22* |
Chicago Fire PDL (PDL) 2, Madison 56ers (NPSL) 0 | Breese Stevens Field; Madison, Wis. | |
| 23 | June 21 |
Real Colorado Foxes (PDL) 1, Kitsap Pumas (PDL) 3 | Bremerton Memorial Stadium; Bremerton, Wash. | |
| 24 | June 21 |
Los Angeles Blues (USL PRO) 1, Ventura County Fusion (PDL) 0 | Ventura College; Ventura, Calif. |
*Game was rescheduled due to weather.
Third Round
| No. | Date | Match | Venue | |
| 25 | June 28 |
FC New York (USL PRO) 1, New York Red Bulls (MLS) 2 | Red Bull Arena; Harrison, N.J. | |
| 26 | June 28 |
Chicago Fire (MLS) 1, Rochester Rhinos (USL PRO) 0 | Sahlen's Stadium; Rochester, N.Y. | |
| 27 | June 28 |
Richmond Kickers (USL PRO) 2, Columbus Crew (MLS) 1 | Columbus Crew Stadium; Columbus, Ohio | |
| 28 | June 28 |
Wilmington Hammerheads (USL PRO) 0, Real Salt Lake (MLS) 2 | Rio Tinto Stadium; Sandy, Utah | |
| 29 | June 28 |
Orlando City Soccer Club (USL PRO) 2, FC Dallas (MLS) 3 | Pizza Hut Park; Frisco, Texas | |
| 30 | June 28 |
Chicago Fire PDL (PDL) 0, Sporting Kansas City (MLS) 3 | LIVESTRONG Sporting Park; Kansas City, Kan. | |
| 31 | June 28 |
Kitsap Pumas (PDL) 1, Seattle Sounders (MLS) 2 | Starfire Sports Stadium; Tukwila, Wash. | |
| 32 | June 28 |
Los Angeles Blues (USL PRO) 1, Los Angeles Galaxy (MLS) 2 | Titan Stadium (CSUF); Fullerton, Calif. |
Quarterfinals
| No. | Date | Match | Venue | |
| 33 | July 12 |
New York Red Bulls (MLS) 0, Chicago Fire (MLS) 4 | Toyota Park; Bridgeview, Ill. | |
| 34 | July 12 |
Richmond Kickers (USL PRO) 2, Sporting Kansas City (MLS) 0 | LIVESTRONG Sporting Park; Kansas City, Kan. | |
| 35 | July 12 |
Real Salt Lake (MLS) 0, FC Dallas (MLS) 2 | Pizza Hut Park; Frisco, Texas | |
| 36 | July 13 |
Los Angeles Galaxy (MLS) 1, Seattle Sounders (MLS) 3 | Starfire Sports Stadium; Tukwila, Wash. |
Semifinals
| No. | Date | Match | Venue |
| 37 | Aug. 30 |
Richmond Kickers (USL PRO) 1, Chicago Fire (MLS) 2 | Toyota Park; Bridgeview, Ill. |
| 38 | Aug. 30 |
FC Dallas (MLS) 0, Seattle Sounders (MLS) 1 | Starfire Sports Stadium; Tukwila, Wash. |
Finals
| No. | Date | Match | Time | Venue |
| 39 | Oct. 4 | Chicago Fire (MLS) at Seattle Sounders (MLS) | 7 p.m. PT | CenturyLink Field; Seattle, Wash. |
