| 07 Jun 23 |
r16        | Charleston BatteryCharleston Ba | 0 - 0 | Detroit City FCDetroit City |
| 10 Jun 23 |
r16        | Loudoun UnitedLoudoun Unite | 3 - 1 | Tulsa RoughnecksTulsa Roughne |
| 10 Jun 23 |
r16        | San Diego LoyalSan Diego Loy | 1 - 1 | Sacramento RepublicSacramento Re |
| 11 Jun 23 |
r16        | Indy ElevenIndy Eleven | 1 - 1 | Hartford AthleticHartford Athl |
| 11 Jun 23 |
r16        | Pittsburgh RiverhoundsPittsburgh Ri | 2 - 0 | Charleston BatteryCharleston Ba |
| 11 Jun 23 |
r16        | Tampa Bay RowdiesTampa Bay Row | 3 - 2 | New Mexico UnitedNew Mexico Un |
| 11 Jun 23 |
r16        | Louisville CityLouisville Ci | 1 - 3 | Memphis 901Memphis 901 |
| 11 Jun 23 |
r16        | Rio Grande ValleyRio Grande Va | 3 - 3 | Miami FCMiami FC |
| 11 Jun 23 |
r16        | Colorado SpringsColorado Spri | 4 - 0 | Orange County SCOrange County |
| 21 Sep 23 |
r16        | Birmingham LegionBirmingham Le | 1 - 1 | Memphis 901Memphis 901 |
| 21 Oct 23 |
r16        | Memphis 901Memphis 901 | 1 - 1 | Louisville CityLouisville Ci |
| 22 Oct 23 |
r16        | Pittsburgh RiverhoundsPittsburgh Ri | 0 - 1 | Detroit City FCDetroit City |
| 22 Oct 23 |
r16        | Tampa Bay RowdiesTampa Bay Row | 0 - 3 | Birmingham LegionBirmingham Le |
| 22 Oct 23 |
r16        | San AntonioSan Antonio | 1 - 0 | Colorado SpringsColorado Spri |
| 22 Oct 23 |
r16        | Sacramento RepublicSacramento Re | 1 - 0 | New Mexico UnitedNew Mexico Un |
| 22 Oct 23 |
r16        | Orange County SCOrange County | 1 - 0 | El Paso LocomotiveEl Paso Locom |
| 22 Oct 23 |
r16        | Charleston BatteryCharleston Ba | 5 - 0 | Indy ElevenIndy Eleven |
| 23 Oct 23 |
r16        | San Diego LoyalSan Diego Loy | 3 - 4 | Phoenix RisingPhoenix Risin |