| 1. Jornada | 08.03.2020 | Memphis 901 | - | Indy Eleven | 2:4 | ||||
| 2. Jornada | 12.07.2020 | Indy Eleven | - | Saint Louis FC | 2:0 |  |
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| 2. Jornada | 19.07.2020 | Indy Eleven | - | Sporting Kansas City 2 | 2:1 | ||||
| 2. Jornada | 23.07.2020 | Pittsburgh Riverhounds | - | Indy Eleven | 0:1 | ||||
| 2. Jornada | 26.07.2020 | Saint Louis FC | - | Indy Eleven | 1:0 |  |
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| 2. Jornada | 30.07.2020 | Indy Eleven | - | Hartford Athletic | 4:1 | ||||
| 3. Jornada | 02.08.2020 | Indy Eleven | - | Sporting Kansas City 2 | 0:1 | ||||
| 3. Jornada | 09.08.2020 | Louisville City FC | - | Indy Eleven | 1:1 | |
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| 3. Jornada | 16.08.2020 | Indy Eleven | - | Pittsburgh Riverhounds | 1:0 | ||||
| 3. Jornada | 27.08.2020 | Louisville City FC | - | Indy Eleven | 1:0 | |
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| 4. Jornada | 06.09.2020 | Indy Eleven | - | Louisville City FC | 1:3 | ||||
| 4. Jornada | 17.09.2020 | Indy Eleven | - | Louisville City FC | 0:2 | ||||
| 4. Jornada | 24.09.2020 | Indy Eleven | - | Saint Louis FC | 1:1 | |
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| 5. Jornada | 01.10.2020 | Indy Eleven | - | Sporting Kansas City 2 | 1:2 | ||||
| 5. Jornada | 04.10.2020 | Saint Louis FC | - | Indy Eleven | 2:1 |
Trinidad y Tobago