First Round
| No. | Date | Match | Venue | |
| 1. | Tue., May 15 8 p.m. ET |
Brooklyn Italians (NPSL) 3, GPS Portland Phoenix (PDL) 2 | Memorial Field, Deering High School Portland, Maine | |
| 2. | Tue., May 15 7 p.m. ET |
Reading United AC (PDL) 2, N.Y. Greek Americans (USASA) 1 | Ray Buss Field, Fleetwood High School Fleetwood, Pa. | |
| 3. | Tue., May 15 7:05 p.m. ET |
Long Island Rough Riders (PDL) 2, FC Sonic (NPSL) 0 | Whitehall High School Stadium Bethlehem, Pa. | |
| 4. | Tue., May 15 7:30 p.m. ET |
Michigan Bucks (PDL) 6, Jersey Shore Boca (USASA) 0 | Ultimate Soccer Pontiac, Mich. | |
| 5. | Tue., May 15 7:30 p.m. ET |
Dulles Sportsplex Aegean Hawks FC (USASA) 3, Carolina Dynamo (PDL) 1 | Maryland SoccerPlex Stadium Boyds, Md. | |
| 6. | Tue., May 15 7 p.m. ET |
Jacksonville United (NPSL) 2, Orlando City U-23s (PDL) 1 | Seminole Soccer Complex Sanford, Fla. | |
| 7. | Tue., May 15 7:30 p.m. ET |
Georgia Revolution (NPSL) 1, Mississippi Brilla FC (PDL) 0 | RYSA Soccerplex Conyers, Ga. | |
| 8. | Tue., May 15 6 p.m. CT |
Chicago Fire PDL (PDL) 1, Croatian Eagles (USASA) 0 | Toyota Park Practice Field Bridgeview, Ill. | |
| 9. | Tue., May 15 7 p.m. CT |
Des Moines Menace (PDL) 3, Milwaukee Bavarians (NPSL) 1 | Bavarian Soccer Park Glendale, Wis. | |
| 10. | Tue., May 15 7 p.m. MT |
K.C. Athletics (USASA) 3, Real Colorado Foxes (PDL) 1 | Colorado School of Mines Soccer Stadium Golden, Colo. | |
| 11. | Tue., May 15 8:15 p.m. CT |
Laredo Heat (PDL) 4, ASC New Stars (USASA) 2 | Texas A&M International University Laredo, Texas | |
| 12. | Tue., May 15 8 p.m. MT |
El Paso Patriots (PDL) 3, NTX Rayados (USASA) 1 | Patriots Stadium El Paso, Texas | |
| 13. | Tue., May 15 7 p.m. PT |
Fresno Fuego (PDL) 2, Stanislaus United Turlock Express (US Club Soccer) 1 | Academica Fields Turlock, Calif. | |
| 14. | Tue., May 15 7:15 p.m. PT |
Ventura County Fusion (PDL) 6, Fullerton Rangers (NPSL) 2 (OT) | Santa Ana Bowl Santa Ana, Calif. | |
| 15. | Tue., May 15 7:30 p.m. PT |
PSA Elite (USASA) 3, Portland Timbers U-23s (PDL) 1 | JELD-WEN Field Portland, Ore. | |
| 16. | Tue., May 15 7:15 p.m. PT |
Cal FC (USASA) 3, at Kitsap Pumas (PDL) 1 | Bremerton Memorial Stadium Bremerton, Wash. |
Second Round
| No. | Date | Match | Venue | |
| 17. | Tue., May 22 7:35 p.m. ET |
Rochester Rhinos (USL PRO) 3, Brooklyn Italians (NPSL) 0 | Sahlen's Stadium Rochester, N.Y. | |
| 18. | Tue., May 22 7:30 p.m. ET |
Charleston Battery (USL PRO) 2, Reading United AC (PDL) 1 | Blackbaud Stadium Charleston, S.C. | |
| 19. | Tue., May 22 7 p.m. ET |
Harrisburg City Islanders (USL PRO) 2, Long Island Rough Riders (PDL) 0 | Skyline Sports Complex Harrisburg, Pa. | |
| 20. | Tue., May 22 7 p.m. ET |
Michigan Bucks (PDL) 1, Pittsburgh Riverhounds (USL PRO) 0 | Chartiers Valley Stadium Bridgeville, Pa. | |
| 21. | Tue., May 22 7:30 p.m. ET |
Richmond Kickers (USL PRO) 4, Dulles Sportsplex Aegean Hawks FC (USASA) 0 | Maryland SportsPlex Stadium Boyds, Md. | |
| 22. | Tue., May 22 7 p.m. ET |
Tampa Bay Rowdies (NASL) 3, Jacksonville United (NPSL) 0 | Patton Park Jacksonville, Fla. | |
| 23. | Tue., May 22 7:30 p.m. ET |
Atlanta Silverbacks (NASL) 1, Georgia Revolution (NPSL) 0 | RYSA Soccerplex Conyers, Ga. | |
| 24. | Tue., May 22 6 p.m. CT |
Dayton Dutch Lions (USL PRO) 2, Chicago Fire PDL (PDL) 1 | Toyota Park Practice Field Bridgeview, Ill. | |
| 25. | Tue., May 22 7:30 p.m. CT |
Minnesota Stars FC (NASL) 2, Des Moines Menace (PDL) 0 | Valley Stadium Des Moines, Iowa | |
| 26. | Tue., May 22 7:30 p.m. ET |
Orlando City Soccer Club (USL PRO) 7, K.C. Athletics (USASA) 0 | Seminole Soccer Complex Sanford, Fla. | |
| 27. | Tue., May 22 7:30 p.m. CT |
San Antonio Scorpions (NASL) 2, Laredo Heat (PDL) 0 | Blossom Athletic Center San Antonio, Texas | |
| 28. | Tue., May 22 8 p.m. MT |
Charlotte Eagles (USL PRO) 1, El Paso Patriots (PDL) 0 | Patriots Stadium El Paso, Texas | |
| 29. | Tue., May 22 7:30 p.m. ET |
Fort Lauderdale Strikers (NASL) 7, Fresno Fuego (PDL) 2 | Lockhart Stadium Fort Lauderdale, Fla. | |
| 30. | Tue., May 22 4 p.m. PT |
Ventura County Fusion (PDL) 3, Los Angeles Blues (USL PRO) 1 (OT) | Hal Shurbeck Field, Fullerton College Fullerton, Calif. | |
| 31. | Tue., May 22 7:07 p.m. ET |
Carolina RailHawks (NASL) 6, PSA Elite (USASA) 0 | WakeMed Soccer Park Cary, N.C. | |
| 32. | Tue., May 22 7 p.m. ET |
Cal FC (USASA) 4, Wilmington Hammerheads (USL PRO) 0 | Legion Sports Complex Wilmington, N.C. |
Third Round
| No. | Date | Match | Venue | |
| 33. | Tue., May 29 |
San Antonio Scorpions (NASL) 1, Houston Dynamo (MLS) 0 | Heroes Stadium San Antonio, Texas | |
| 34. | Tue., May 29 7:30 p.m. ET |
Michigan Bucks (PDL) 3, Chicago Fire (MLS) 2 (OT) | Ultimate Soccer Pontiac, Mich. | |
| 35. | Tue., May 29 7:30 p.m. CT |
Sporting Kansas City (MLS) 3, Orlando City Soccer Club (USL PRO) 2 | LIVESTRONG Sporting Park Kansas City, Kan. | |
| 36. | Tue., May 29 7 p.m. ET |
D.C. United (MLS) 2, Richmond Kickers (USL PRO) 1 (OT) | Richmond City Stadium Richmond, Va. | |
| 37. | Tue., May 29 7:30 p.m. ET |
Dayton Dutch Lions (USL PRO) 2, Columbus Crew (MLS) 1 | Columbus Crew Stadium Columbus, Ohio | |
| 38. | Tue., May 29 7:30 p.m. CT |
Charlotte Eagles (USL PRO) 2, FC Dallas (MLS) 0 | FC Dallas Stadium Frisco, Texas | |
| 39. | Tue., May 29 7:30 p.m. PT |
San Jose Earthquakes (MLS) 2, Fort Lauderdale Strikers (NASL) 1 | Cagan Stadium, Stanford University Stanford, Calif. | |
| 40. | Tue., May 29 7:30 p.m. ET |
Philadelphia Union (MLS) 3, Rochester Rhinos (USL PRO) 0 | PPL Park Chester, Pa. | |
| 41. | Tue., May 29 7 p.m. ET |
Harrisburg City Islanders (USL PRO) 4, New England Revolution (MLS) 3 (SO) | Skyline Sports Complex Harrisburg, Pa. | |
| 42. | Tue., May 29 7:30 p.m. ET |
New York Red Bulls (MLS) 3, Charleston Battery (USL PRO) 0 | Blackbaud Stadium Charleston, S.C. | |
| 43. | Tue., May 29 7 p.m. PT |
Chivas USA (MLS) 1, Ventura County Fusion (PDL) 0 | Ventura College Charleston, S.C. | |
| 44. | Tue., May 29 7:07 p.m. ET |
Carolina RailHawks (NASL) 2, LA Galaxy (MLS) 1 | WakeMed Soccer Park Cary, N.C. | |
| 45. | Tue., May 29 7:30 p.m. ET |
Colorado Rapids (MLS) 3, Tampa Bay Rowdies (NASL) 1 | Al Lang Stadium St. Petersburg, Fla. | |
| 46. | Wed., May 30 7:30 p.m. PT |
Cal FC (USASA) 1, Portland Timbers (MLS) 0 (OT) | JELD-WEN Field Portland, Ore. | |
| 47. | Wed., May 30 7 p.m. PT |
Seattle Sounders (MLS) 5, Atlanta Silverbacks (NASL) 1 | Starfire Sports Complex Tukwila, Wash. | |
| 48. | Tue., May 29 7 p.m. MT |
Minnesota Stars FC (NASL) 3, Real Salt Lake (MLS) 1 | Rio Tinto Stadium Sandy, Utah |
Fourth Round
| No. | Date | Match | Venue | |
| 49. | Tue., June 5 |
Harrisburg City Islanders (USL PRO) 3, New York Red Bulls (MLS) 1 (OT) | Skyline Sports Complex Harrisburg, Pa. | |
| 50. | Tue., June 5 |
Philadelphia Union (MLS) 2, D.C. United (MLS) 1 (OT) | Maryland SoccerPlex Boyds, Md. | |
| 51. | Tue., June 5 |
Dayton Dutch Lions (USL PRO) 2, Michigan Bucks (PDL) (OT) | Oakland University Soccer Field Rochester, Mich. | |
| 52. | Tue., June 5 |
Sporting Kansas City (MLS) 2, Colorado Rapids (MLS) 0 | LIVESTRONG Sporting Park Kansas City, Kan. | |
| 53. | Tue., June 5 |
Charlotte Eagles (USL PRO) 2, San Antonio Scorpions (NASL) 1 (OT) | Heroes Stadium San Antonio, Texas | |
| 54. | Tue., June 5 |
San Jose Earthquakes (MLS) 1, Minnesota Stars FC (NASL) 0 | Cagan Stadium, Stanford University Stanford, Calif. | |
| 55. | Tue., June 5 |
Seattle Sounders FC (MLS) 5, Cal FC (USASA) 0 | Starfire Sports Complex Tukwila, Wash. | |
| 56. | Tue., June 5 |
Chivas USA (MLS) 2, Carolina RailHawks (NASL) 1 | WakeMed Soccer Park Cary, N.C. |
Quarterfinals
| No. | Date | Match | Venue | |
| 57. |
Tue., June 26 |
Philadelphia Union (MLS) 5, Harrisburg City Islanders (USL PRO) 2 | PPL Park Chester, Pa. |
|
| 58. |
Tue., June 26 |
Sporting Kansas City (MLS) 3, Dayton Dutch Lions (USL PRO) 0 | LIVESTRONG Sporting Park Kansas City, Kan. |
|
| 59. |
Tue., June 26 |
Chivas USA (MLS) 2, Charlotte Eagles (USL PRO) 1 | Titan Stadium, Cal State Fullerton Fullerton, Calif. |
|
| 60. |
Tue., June 26 |
Seattle Sounders FC (MLS)1, San Jose Earthquakes (MLS) 0 | Kezar Stadium San Francisco, Calif. |
Semifinals
| No. | Date | Match | Venue | |
| 61. |
Wed., July 11 |
Sporting Kansas City (MLS) 2, Philadelphia Union (MLS) 0 | PPL Park Chester, Pa. |
|
| 62. |
Wed., July 11 |
Seattle Sounders FC (MLS) 4, Chivas USA (MLS) 1 | Starfire Sports Complex Tukwila, Wash. |
Finals
| No. | Date | Match | Venue | |
| 63. |
Wed., Aug. 8 |
Sporting Kansas City (MLS) 1, Seattle Sounders FC (MLS) 1; SKC wins shootout 3-2 | LIVESTRONG Sporting Park; Kansas City, Kan. |
