| ROUND | R1 | R2 | R3 | R4 | R5 | QF | SF | F |
| Season archive |
| Tuesday, 11 June 2019 | ||||||
| r4 | Houston Dynamo | 3-2 | Austin Bold | |||
| 14 | Martínez | 48 | Báez | |||
| 31 | Peña | 58 | Promise | |||
| 40 | Vera | |||||
| r4 | New York Red Bulls | 2-3 | New England Revolution | aet | ||
| 19 | Barlow | 1 | Agudelo | |||
| 54 | Cásseres | 85 | Bunbury | |||
| 109 | Bunbury | |||||
| r4 | Columbus Crew | 1-0 | Pittsburgh Riverhounds | |||
| 55 | Accam | |||||
| r4 | Real Salt Lake | 0-3 | Los Angeles | |||
| 8 | Vela | |||||
| 64 | Nguyen | |||||
| 90 | Diomande | |||||
| r4 | San Jose Earthquakes | 4-3 | Sacramento Republic | |||
| 10 | Eriksson | 2 | Werner | |||
| 38(p) | Espinoza | 14 | Bijev | |||
| 78 | Qazaishvili | 90 | Skundrich | |||
| 90 | Qazaishvili | |||||
| r4 | Saint Louis | 2-1 | Chicago Fire | |||
| 17 | Martz | 72(p) | Nikolić | |||
| 21 | Abend | |||||
| Wednesday, 12 June 2019 | ||||||
| r4 | D.C. United | 2-1 | Philadelphia Union | aet | ||
| 118 | McCann | 113 | Fontana | |||
| 120(p) | Rooney | |||||
| r4 | FC Dallas | 4-0 | OKC Energy | |||
| 11 | Hedges | |||||
| 43 | Barrios | |||||
| 52 | Badji | |||||
| 90(p) | Ziegler | |||||
| r4 | Colorado Rapids | 2-2 | New Mexico United | aet, p2-4 | ||
| 35 | Rubio | 3 | Sandoval | |||
| 46 | Mezquida | 94 | Frater | |||
| r4 | LA Galaxy | 3-0 | Orange County FC | |||
| 55 | Álvarez | |||||
| 61 | Álvarez | |||||
| 90 | Cuello | |||||
| r4 | Seattle Sounders | 1-2 | Portland Timbers | |||
| 44 | Víctor | 6 | Fernández | |||
| 50 | Fernández | |||||
| r4 | Minnesota United | 4-1 | Sporting Kansas City | |||
| 2 | Rodríguez | 27 | Gerso | |||
| 46 | Finlay | |||||
| 55 | Quintero | |||||
| 67 | Quintero | |||||
| r4 | New York City | 4-0 | North Carolina | |||
| 25(og) | Guillén | |||||
| 45 | Medina | |||||
| 52 | Parks | |||||
| 76 | Parks | |||||
| r4 | FC Cincinnati | 2-1 | Louisville City | aet | ||
| 23 | Adi | 30 | Mkosana | |||
| 103 | Manneh | |||||
| r4 | Memphis 901 | 1-3 | Orlando City | |||
| 50 | Collier | 38(p) | Kljestan | |||
| 55 | Kljestan | |||||
| 71 | Jansson | |||||
| Thursday, 13 June 2019 | ||||||
| r4 | Atlanta United | 3-1 | Charleston Battery | aet | ||
| 79 | Williams | 20 | Svantesson | |||
| 110 | Vázquez | |||||
| 120 | Vázquez | |||||
| 4 | Charles BOATENG (Richmond Kickers) | |
| 3 | +1 | Devon SANDOVAL (New Mexico United) |
| +1 | Ian SVANTESSON (Charleston Battery) | |
| Brandon ALLEN (Tampa Bay Rowdies) | ||
| ANDRÉ Luíz LIMA (Austin Bold) | ||
| Or BAROUCH (Cal FC) | ||
| 2 | +1 | Sam WERNER (Sacramento Republic) |
| Josh MORTON (Memphis 901) | ||
| +2 | Brian FERNÁNDEZ (Portland Timbers) | |
| Adrian BILLHARDT () | ||
| +2 | Brandon VÁZQUEZ (Atlanta United) | |
| +1 | Kevaughn FRATER (New Mexico United) | |
| Jeremy RAFANELLO (Reading United) | ||
| +2 | Teal BUNBURY (New England Revolution) | |
| +2 | Keaton PARKS (New York City) | |
| Neco BRETT (Pittsburgh Riverhounds) | ||
| +2 | Sacha KLJESTAN (Orlando City) | |
| +2 | Efrain ÁLVAREZ (LA Galaxy) | |
| +2 | Valeri QAZAISHVILI (San Jose Earthquakes) | |
| Sonny GUADARRAMA (Austin Bold) | ||
| Jochen GRAF (Memphis 901) | ||
| Bljedi BARDIĆ (New York Cosmos) | ||
| Christian EISSELE (OKC Energy) | ||
| +1 | Guy ABEND (Saint Louis) | |
| Robbie KRISTO (North Carolina) | ||
| +2 | Darwin QUINTERO (Minnesota United) | |
| Elma N'FOR (Lansing Ignite) | ||
| Dakota COLLINS (Orange County FC) | ||
| Jiro BARRIGA TOYAMA (Forward Madison) |