1. Round | 02/03/2019 | Orlando City | - | New York City FC | 2:2 | ||||
1. Round | 16/03/2019 | Orlando City | - | Impact de Montréal | 1:3 | ||||
2. Round | 14/04/2019 | Real Salt Lake | - | Orlando City | 2:1 | ||||
3. Round | 04/05/2019 | Orlando City | - | Toronto FC | 0:2 | ||||
3. Round | 12/05/2019 | Atlanta United FC | - | Orlando City | 1:0 | ||||
3. Round | 16/05/2019 | Seattle Sounders | - | Orlando City | 2:1 | ||||
3. Round | 19/05/2019 | Orlando City | - | FC Cincinnati | 5:1 | ||||
3. Round | 25/05/2019 | Orlando City | - | Los Angeles Galaxy | 0:1 |