First Round
June 20 in High Point, N.C. Carolina Dynamo (D3) 1 Milwaukee Bavarian Leinenkugel (USASA) 0. Goal: Haupt (Dudley) 86. Carolina — Powell, Ronemus, Freeman, Atta, Collins, Haupt, Duff (Fedor, 68), Dudley, Breslin (Rice, 46), Espindola, Hamid (Upchurch, 89). Leinenkugel — Howard, Passelt, Pearson, Eichman, Gansler, Hospel, Schweinert, Kreitmer, Zaiss, Stempinski (Troskey, 85), Votja (Cartledge, 46). Red card: Carolina — Fedor 77. Att.: n/a.First-Round Results
| Date | Result |
| June 5 | Wilmington Hammerheads (D3) 8 Tulsa Los Lobos (USASA) 1 |
| June 8 | Mid Michigan Bucks (PDL) 3 Austin Lone Stars (D3) 2 |
| June 9 | Cape Cod Crusaders (D3) 1 New York Freedoms (PDL) 3 |
| June 9 | New Jersey Stallions (D3) 1 United German-Hungarians (USASA) 2 |
| June 10 | No. Virginia Royals (D3) 3 Cocoa Expos (PDL) 5 |
| June 11 | Arizona Sahuaros (D3) 3 Fresno Mexico SC (USASA) 2 (OT) |
| June 16 | Chico Rooks (D3) 2 Spokane Shadow (PDL) 3 (OT) |
| June 20 | Carolina Dynamo (D3) 1 Milwaukee Bavarian Leinenkugel (USASA) 0 |
Second-Round Schedule
| Date | Matchup | Kickoff (local time) |
| June 23 | United German-Hungarians (USASA) at Staten Island Vipers (A-League) | 7:30 p.m. |
| June 23 | Mid Michigan Bucks (PDL) at Minnesota Thunder (A-League) | 7:30 p.m. |
| June 23 | Spokane Shadow (PDL) at Seattle Sounders (A-League) | 7:30 p.m. |
| June 30 | New York Freedoms (PDL) at Rochester Rhinos (A-League) | 7:30 p.m. |
| June 30 | Arizona Sahuaros (D3) at San Diego Flash (A-League) | 4:15 p.m. |
| July 6 | Wilmington Hammerheads (D3) at Charleston Battery (A-League) | 8:00 p.m. |
| July 10 | Cocoa Expos (PDL) at Jacksonville Cyclones (A-League) | 7:30 p.m. |
| TBA | Carolina Dynamo (D3) at Orange County Zodiac (A-League) | TBA |