| ROUND | R1 | R2 | R3 | R4 | R5 | QF | SF | F |
| Season archive |
| Tuesday, 14 May 2019 | ||||||
| r2 | Pittsburgh Riverhounds | 3-0 | Dayton Dutch Lions | |||
| 57(p) | Brett | |||||
| 69 | Brett | |||||
| 90 | Velarde | |||||
| r2 | Tampa Bay Rowdies | 4-1 | Brave SC | |||
| 43 | Koné | 89 | ||||
| 45 | Steinberger | |||||
| 62 | Allen | |||||
| 90 | Taylor | |||||
| r2 | San Antonio | 2-0 | Laredo Heat | |||
| 17 | Eboussi | |||||
| 41 | Guzmán | |||||
| r2 | Nashville | 3-2 | Tormenta FC-2 | |||
| 8 | Mensah | 43 | Billhardt | |||
| 32 | Winn | 68 | ||||
| 52 | Lancaster | |||||
| r2 | OKC Energy | 3-1 | NTX Rayados | |||
| 51 | Sasivarevic | 62 | ||||
| 81(p) | Eissele | |||||
| 90(p) | Watson | |||||
| r2 | Charlotte Independence | 2-2 | Florida Soccer Soldiers | aet, p4-5 | ||
| 31 | Roberts | 78 | ||||
| 92 | Oduro | 119 | Sabella | |||
| r2 | Las Vegas Lights | 2-0 | Cal FC | |||
| 13 | Ochoa | |||||
| 50 | Rojas | |||||
| r2 | Austin Bold | 2-0 | FC Tulsa | |||
| 34 | Guadarrama | |||||
| 74 | André Lima | |||||
| r2 | Hartford Athletic | 2-1 | New York Cosmos | |||
| 16 | Swartz | 57 | Bardić | |||
| 25 | Jørgensen | |||||
| Wednesday, 15 May 2019 | ||||||
| r2 | North Carolina | 4-1 | Richmond Kickers | |||
| 16 | Fortune | 34 | Ackwei | |||
| 52 | Kristo | |||||
| 61(p) | Kristo | |||||
| 70 | Chester | |||||
| r2 | Orange County SC | 2-2 | Orange County FC | aet, p3-5 | ||
| 13(og) | 27 | Collins | ||||
| 87 | Jones | 92 | ||||
| r2 | Phoenix Rising | 2-2 | New Mexico United | aet, p3-4 | ||
| 65(p) | Flemmings | 79 | Sandoval | |||
| 101 | Jahn | 95 | Sandoval | |||
| r2 | Indy Eleven | 1-0 | Lansing Ignite | |||
| 57 | Enevoldsen | |||||
| r2 | Sacramento Republic | 1-0 | Reno 1868 | |||
| 82 | Werner | |||||
| r2 | Des Moines Menace | 1-1 | Saint Louis | aet, p1-3 | ||
| 39(p) | Perea | 14 | Greig | |||
| r2 | Colorado Springs | 1-0 | FC Denver | |||
| 45 | Donsu | |||||
| r2 | Louisville City | 3-0 | Reading United | |||
| 12 | Thiam | |||||
| 19 | Davis | |||||
| 88 | Jane | |||||
| r2 | El Paso Locomotive | 0-3 | Forward Madison | |||
| 19 | Barriga Toyama | |||||
| 26 | Díaz | |||||
| 76 | Michaud | |||||
| r2 | Birmingham Legion | 4-1 | West Chester United | |||
| 22(p) | Hoffman | 61 | ||||
| 38 | Hollinger-Janzen | |||||
| 51 | Kasim | |||||
| 89 | Opoku | |||||
| r2 | Memphis 901 | 3-1 | New York U23 | |||
| 8 | Lindley | 5 | ||||
| 26 | Morton | |||||
| 73 | Morton | |||||
| r2 | Greenville Triumph | 1-2 | Charleston Battery | |||
| 29 | Hemmings | 79 | Svantesson | |||
| 90 | Svantesson | |||||
| r2 | El Farolito | 0-1 | Fresno FC | |||
| 75 | Lawal | |||||
| 4 | Charles BOATENG (Richmond Kickers) | |
| 3 | Or BAROUCH (Cal FC) | |
| 2 | +2 | Josh MORTON (Memphis 901) |
| +2 | Devon SANDOVAL (New Mexico United) | |
| +1 | Adrian BILLHARDT () | |
| +1 | Bljedi BARDIĆ (New York Cosmos) | |
| +2 | Robbie KRISTO (North Carolina) | |
| +2 | Ian SVANTESSON (Charleston Battery) | |
| Elma N'FOR (Lansing Ignite) | ||
| Jeremy RAFANELLO (Reading United) | ||
| +2 | Neco BRETT (Pittsburgh Riverhounds) | |
| +1 | Jiro BARRIGA TOYAMA (Forward Madison) |