1. Round | 23/03/2019 | New York RB | - | Orlando City | 0:1 | ||||
2. Round | 31/03/2019 | Orlando City | - | D.C. United | 1:2 | ||||
2. Round | 07/04/2019 | Orlando City | - | Colorado Rapids | 4:3 | ||||
2. Round | 14/04/2019 | Real Salt Lake | - | Orlando City | 2:1 | ||||
2. Round | 20/04/2019 | Orlando City | - | Vancouver Whitecaps | 1:0 | ||||
2. Round | 27/04/2019 | New York City FC | - | Orlando City | 1:1 | ||||
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 | ||||
4. Round | 01/06/2019 | Impact de Montréal | - | Orlando City | 0:3 | ||||
5. Round | 22/07/2019 | Orlando City | - | New York RB | 0:1 | ||||
5. Round | 28/07/2019 | New England Revolution | - | Orlando City | 4:1 | ||||
6. Round | 04/08/2019 | Orlando City | - | FC Dallas | 2:0 | ||||
7. Round | 29/09/2019 | FC Cincinnati | - | Orlando City | 1:1 |