| 1. Round | 12/03/2023 | Orange County SC | - | Louisville City FC | 1:3 |  |
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| 1. Round | 19/03/2023 | Monterey Bay FC | - | Louisville City FC | 0:1 | ||||
| 1. Round | 25/03/2023 | Louisville City FC | - | El Paso Locomotive | 0:3 | ||||
| 2. Round | 02/04/2023 | Sacramento Republic | - | Louisville City FC | 5:0 | ||||
| 2. Round | 08/04/2023 | Louisville City FC | - | Detroit City FC | 1:0 | ||||
| 2. Round | 16/04/2023 | Louisville City FC | - | San Antonio FC | 1:0 | ||||
| 2. Round | 23/04/2023 | Charleston Battery | - | Louisville City FC | 0:0 | ||||
| 3. Round | 25/05/2023 | Louisville City FC | - | FC Tulsa | 1:2 | ||||
| 4. Round | 04/06/2023 | Hartford Athletic | - | Louisville City FC | 0:0 |  |
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| 4. Round | 11/06/2023 | Louisville City FC | - | Memphis 901 | 1:3 | ||||
| 4. Round | 18/06/2023 | Phoenix Rising | - | Louisville City FC | 2:2 | ||||
| 4. Round | 25/06/2023 | Louisville City FC | - | Las Vegas Lights FC | 1:0 | |
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| 5. Round | 02/07/2023 | Pittsburgh Riverhounds | - | Louisville City FC | 0:0 | ||||
| 5. Round | 09/07/2023 | Louisville City FC | - | Loudoun United | 1:0 | ||||
| 5. Round | 13/07/2023 | Louisville City FC | - | Pittsburgh Riverhounds | 0:1 | ||||
| 8. Round | 15/10/2023 | Louisville City FC | - | Tampa Bay Rowdies | 2:3 |
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