2. Round
15/05/2019 00:00 Pittsburgh Riverhounds - Dayton Dutch Lions 3:0 (0:0)
00:00 Tampa Bay Rowdies - The Villages SC 4:1 (2:0)
00:00 Charlotte Independence - Florida Soccer Soldiers 4:5 (1:0, 1:1, 2:2) pso
00:30 Hartford Athletic - New York Cosmos II 2:1 (2:0)
01:30 Nashville SC - Tormenta FC II 3:2 (2:1)
01:30 OKC Energy FC - NTX Rayados 3:1 (0:0)
01:30 Austin Bold - Tulsa Roughnecks 2:0 (1:0)
01:30 San Antonio FC - Laredo Heat 2:0 (2:0)
03:30 Las Vegas Lights FC - Cal FC 2:0 (1:0)
22:30 El Farolito SC - Fresno FC 0:1 (0:0)
16/05/2019 00:00 North Carolina FC - Richmond Kickers 4:1 (1:1)
00:00 Louisville City FC - Reading United 3:0 (2:0)
00:00 Indy Eleven - Lansing Ignite 1:0 (0:0)
00:00 Greenville Triumph SC - Charleston Battery 1:2 (1:0)
01:00 Memphis 901 - New York RB III 3:1 (2:1)
01:00 Birmingham Legion - West Chester United Predators 4:1 (2:0)
01:30 Des Moines Menace - Saint Louis FC 1:3 (1:1, 1:1, 1:1) pso
02:00 El Paso Locomotive - Forward Madison FC 0:3 (0:2)
02:00 Colorado Springs Switchbacks - FC Denver 1:0 (1:0)
03:30 Sacramento Republic - Reno 1868 FC 1:0 (0:0)
03:30 Orange County SC - Orange County FC 3:5 (1:1, 2:2, 2:2) pso
03:30 Phoenix Rising - New Mexico United 3:4 (0:0, 1:1, 2:2) pso
3. Round
29/05/2019 01:30 OKC Energy FC - Tampa Bay Rowdies 4:3 (3:2)
30/05/2019 00:00 North Carolina FC - Florida Soccer Soldiers 1:0 (0:0)
00:00 Louisville City FC - Birmingham Legion 1:0 (0:0)
00:45 Pittsburgh Riverhounds - Indy Eleven 1:0 (0:0)
01:00 Saint Louis FC - Forward Madison FC 3:1 (2:1)
01:00 Memphis 901 - Hartford Athletic 4:0 (2:0)
01:30 Nashville SC - Charleston Battery 0:3 (0:1, 1:1, 1:1) pso
01:30 Austin Bold - San Antonio FC 4:2 (3:1)
02:00 Colorado Springs Switchbacks - New Mexico United 1:2 (0:0, 1:1) aet
03:30 Las Vegas Lights FC - Orange County FC 3:5 (1:3)
03:30 Sacramento Republic - Fresno FC 1:0 (0:0, 0:0) aet
4. Round
12/06/2019 00:00 Columbus Crew - Pittsburgh Riverhounds 1:0 (0:0)
00:30 New York RB - New England Revolution 2:3 (1:1, 2:2) aet
01:00 Houston Dynamo - Austin Bold 3:2 (3:0)
01:30 Saint Louis FC - Chicago Fire 2:1 (2:0)
03:00 Real Salt Lake - Los Angeles FC 0:3 (0:1)
03:30 San Jose Earthquakes - Sacramento Republic 4:3 (2:2)
13/06/2019 00:00 New York City FC - North Carolina FC 4:0 (2:0)
00:00 D.C. United - Philadelphia Union 2:1 (0:0, 0:0) aet
00:30 FC Cincinnati - Louisville City FC 2:1 (1:1, 1:1) aet
01:00 Minnesota United FC - Sporting Kansas City 4:1 (1:1)
01:00 FC Dallas - OKC Energy FC 4:0 (2:0)
01:30 Memphis 901 - Orlando City 1:3 (0:1)
02:00 Colorado Rapids - New Mexico United 2:4 (1:1, 2:2, 2:2) pso
03:30 Los Angeles Galaxy - Orange County FC 3:0 (0:0)
03:30 Seattle Sounders - Portland Timbers 1:2 (1:1)
14/06/2019 00:00 Atlanta United FC - Charleston Battery 3:1 (0:1, 1:1) aet
Round of 16
19/06/2019 00:00 Houston Dynamo - Minnesota United FC 2:3 (2:0)
00:00 Columbus Crew - Atlanta United FC 2:3 (1:2)
20/06/2019 00:00 D.C. United - New York City FC 1:2 (1:2)
00:30 Orlando City - New England Revolution 2:1 (0:0, 0:0) aet
01:00 FC Dallas - New Mexico United 1:2 (1:1)
01:30 Saint Louis FC - FC Cincinnati 1:0 (0:0)
04:00 Portland Timbers - Los Angeles Galaxy 4:0 (3:0)
21/06/2019 03:30 Los Angeles FC - San Jose Earthquakes 3:1 (1:1)
Quarter-finals
11/07/2019 00:30 Orlando City - New York City FC 5:4 (0:0, 1:1, 1:1) pso
00:30 Atlanta United FC - Saint Louis FC 2:0 (0:0)
01:00 Minnesota United FC - New Mexico United 6:1 (5:1)
03:30 Los Angeles FC - Portland Timbers 0:1 (0:0)
Semi-finals
07/08/2019 00:30 Orlando City - Atlanta United FC 0:2 (0:1)
08/08/2019 01:00 Minnesota United FC - Portland Timbers 2:1 (1:1)
Final
28/08/2019 01:00 Atlanta United FC - Minnesota United FC 2:1 (2:0)