| 18 Mar 24 | r00    | Chattanooga FCChattanooga F | 0 - 1 | Miami UnitedMiami United |
| 19 Mar 24 | r00 | Richmond KickersRichmond Kick | 1 - 0 | Christos FCChristos FC |
| 19 Mar 24 | r00 | Vermont Green FCVermont Green | 4 - 3 | Lexington SCLexington SC |
| 19 Mar 24 | r00 | The Villages SCThe Villages | 0 - 2 | Savannah CloversSavannah Clov |
| 19 Mar 24 | r00 | West Chester United SCWest Chester | 0 - 2 | Maryland Bobcats FCMaryland Bobc |
| 20 Mar 24 | r00 | Tulsa AthleticsTulsa Athleti | 1 - 4 | Northern Colorado HailstoNorthern Colo |
| 20 Mar 24 | r00 | Portland Timbers IIPortland Timb | 1 - 2 | El FarolitoEl Farolito |
| 20 Mar 24 | r00 | SC United BantamsSC United Ban | 0 - 1 | Greenville Triumph SCGreenville Tr |
| 20 Mar 24 | r00 | Asheville City SCAsheville Cit | 0 - 2 | One Knoxville SCOne Knoxville |
| 20 Mar 24 | r00 | New York RB IINew York RB I | 5 - 1 | Hudson Valley HammersHudson Valley |
| 21 Mar 24 | r00 | Chicago Fire IIChicago Fire | 6 - 0 | Chicago City SCChicago City |
| 21 Mar 24 | r00 | Chicago House ACChicago House | 0 - 3 | Minnesota United FC 2Minnesota Uni |
| 21 Mar 24 | r00 | Capo FCCapo FC | 2 - 2 | Des Moines MenaceDes Moines Me |
| 21 Mar 24 | r00 | Ballard FCBallard FC | 0 - 1 | Spokane VelocitySpokane Veloc |
| 21 Mar 24 | r00 | FC MotownFC Motown | 0 - 3 | New York City FC IINew York City |
| 21 Mar 24 | r00 | Chattanooga Red Wolves SCChattanooga R | 4 - 2 | Brockton FC UnitedBrockton FC U |
| 21 Mar 24 | r00 | Western Mass PioneersWestern Mass | 0 - 4 | Union OmahaUnion Omaha |
| 21 Mar 24 | r00 | Carolina CoreCarolina Core | 3 - 2 | Northern Virginia FCNorthern Virg |
| 22 Mar 24 | r00 | Colorado Rapids 2Colorado Rapi | 3 - 0 | AztecaAzteca |
| 02 Apr 24 | r00 | Richmond KickersRichmond Kick | 5 - 2 | Maryland Bobcats FCMaryland Bobc |
| 02 Apr 24 | r00 | New York City FC IINew York City | 4 - 2 | New York RB IINew York RB I |
| 03 Apr 24 | r00 | Minnesota United FC 2Minnesota Uni | 0 - 2 | Michigan Stars FCMichigan Star |
| 03 Apr 24 | r00 | Central Valley Fuego FCCentral Valle | 1 - 2 | El FarolitoEl Farolito |
| 03 Apr 24 | r00 | Miami UnitedMiami United | 2 - 0 | Club de LyonClub de Lyon |
| 03 Apr 24 | r00  | One Knoxville SCOne Knoxville | 2 - 3 | Greenville Triumph SCGreenville Tr |
| 03 Apr 24 | r00 | Vermont Green FCVermont Green | 1 - 2 | Carolina CoreCarolina Core |
| 03 Apr 24 | r00 | Tormenta FCTormenta FC | 4 - 0 | Savannah CloversSavannah Clov |
| 04 Apr 24 | r00 | Chicago Fire IIChicago Fire | 2 - 0 | Forward Madison FCForward Madis |
| 04 Apr 24 | r00 | Union OmahaUnion Omaha | 3 - 1 | Des Moines MenaceDes Moines Me |
| 04 Apr 24 | r00 | Colorado Rapids 2Colorado Rapi | 2 - 3 | Northern Colorado HailstoNorthern Colo |
| 04 Apr 24 | r00 | Spokane VelocitySpokane Veloc | 1 - 0 | LA ForceLA Force |
| 04 Apr 24 | r00 | Ventura CountyVentura Count | 0 - 3 | Irvine ZetaIrvine Zeta |
| 16 Apr 24 | r00 | Louisville CityLouisville Ci | 3 - 1 | Greenville Triumph SCGreenville Tr |
| 16 Apr 24 | r00 | Detroit City FCDetroit City | 1 - 0 | Michigan Stars FCMichigan Star |
| 16 Apr 24 | r00 | Charlotte IndependenceCharlotte Ind | 4 - 4 | Rhode Island FCRhode Island |
| 17 Apr 24 | r00 | Oakland RootsOakland Roots | 2 - 1 | El FarolitoEl Farolito |
| 17 Apr 24 | r00 | Hartford AthleticHartford Athl | 2 - 3 | New York City FC IINew York City |
| 17 Apr 24 | r00 | Richmond KickersRichmond Kick | 0 - 0 | Loudoun UnitedLoudoun Unite |
| 17 Apr 24 | r00 | North Carolina FCNorth Carolin | 1 - 0 | Carolina CoreCarolina Core |
| 17 Apr 24 | r00 | Miami FCMiami FC | 2 - 4 | Tormenta FCTormenta FC |
| 17 Apr 24 | r00 | Memphis 901Memphis 901 | 2 - 0 | Miami UnitedMiami United |
| 18 Apr 24 | r00 | Birmingham LegionBirmingham Le | 4 - 2 | Chattanooga Red Wolves SCChattanooga R |
| 18 Apr 24 | r00 | Chicago Fire IIChicago Fire | 0 - 1 | Indy ElevenIndy Eleven |
| 18 Apr 24 | r00 | Tulsa RoughnecksTulsa Roughne | 2 - 1 | Northern Colorado HailstoNorthern Colo |
| 18 Apr 24 | r00 | Union OmahaUnion Omaha | 0 - 0 | El Paso LocomotiveEl Paso Locom |
| 18 Apr 24 | r00 | Las Vegas LightsLas Vegas Lig | 2 - 1 | Spokane VelocitySpokane Veloc |
| 18 Apr 24 | r00 | Monterey Bay FCMonterey Bay | 2 - 1 | Irvine ZetaIrvine Zeta |
| |
| 07 May 24 | r32 | Pittsburgh RiverhoundsPittsburgh Ri | 0 - 1 | Tulsa RoughnecksTulsa Roughne |
| 07 May 24 | r32 | Atlanta UnitedAtlanta Unite | 3 - 0 | Charlotte IndependenceCharlotte Ind |
| 08 May 24 | r32 | Houston DynamoHouston Dynam | 3 - 3 | Detroit City FCDetroit City |
| 08 May 24 | r32 | FC DallasFC Dallas | 1 - 0 | Memphis 901Memphis 901 |
| 08 May 24 | r32 | San Jose EarthquakesSan Jose Eart | 1 - 0 | Oakland RootsOakland Roots |
| 08 May 24 | r32 | Orange County SCOrange County | 1 - 2 | Loudoun UnitedLoudoun Unite |
| 08 May 24 | r32 | Sacramento RepublicSacramento Re | 2 - 0 | Monterey Bay FCMonterey Bay |
| 08 May 24 | r32 | Charleston BatteryCharleston Ba | 3 - 2 | Tormenta FCTormenta FC |
| 08 May 24 | r32 | North Carolina FCNorth Carolin | 1 - 2 | Phoenix RisingPhoenix Risin |
| 08 May 24 | r32 | Indy ElevenIndy Eleven | 2 - 0 | San AntonioSan Antonio |
| 08 May 24 | r32 | Tampa Bay RowdiesTampa Bay Row | 6 - 4 | Birmingham LegionBirmingham Le |
| 08 May 24 | r32 | New York City FC IINew York City | 1 - 0 | Colorado SpringsColorado Spri |
| 09 May 24 | r32 | Union OmahaUnion Omaha | 1 - 2 | Sporting Kansas CitySporting Kans |
| 09 May 24 | r32 | New Mexico UnitedNew Mexico Un | 4 - 2 | Real Salt LakeReal Salt Lak |
| 09 May 24 | r32 | Seattle Sounders FCSeattle Sound | 2 - 2 | Louisville CityLouisville Ci |
| 09 May 24 | r32 | Las Vegas LightsLas Vegas Lig | 1 - 3 | Los Angeles FCLos Angeles F |
| |
| 21 May 24 | r16 | Charleston BatteryCharleston Ba | 0 - 0 | Atlanta UnitedAtlanta Unite |
| 21 May 24 | r16 | New York City FC IINew York City | 0 - 3 | New Mexico UnitedNew Mexico Un |
| 22 May 24 | r16 | Sporting Kansas CitySporting Kans | 4 - 0 | Tulsa RoughnecksTulsa Roughne |
| 22 May 24 | r16 | Sacramento RepublicSacramento Re | 4 - 3 | San Jose EarthquakesSan Jose Eart |
| 22 May 24 | r16 | Los Angeles FCLos Angeles F | 3 - 0 | Loudoun UnitedLoudoun Unite |
| 22 May 24 | r16 | Indy ElevenIndy Eleven | 3 - 0 | Detroit City FCDetroit City |
| 22 May 24 | r16 | Tampa Bay RowdiesTampa Bay Row | 1 - 2 | FC DallasFC Dallas |
| 23 May 24 | r16 | Seattle Sounders FCSeattle Sound | 2 - 1 | Phoenix RisingPhoenix Risin |
| |
| 09 Jul 24 | QF | Atlanta UnitedAtlanta Unite | 1 - 2 | Indy ElevenIndy Eleven |
| 10 Jul 24 | QF | Sacramento RepublicSacramento Re | 1 - 2 | Seattle Sounders FCSeattle Sound |
| 11 Jul 24 | QF | Sporting Kansas CitySporting Kans | 2 - 1 | FC DallasFC Dallas |
| 11 Jul 24 | QF | Los Angeles FCLos Angeles F | 3 - 1 | New Mexico UnitedNew Mexico Un |
| |
| 28 Aug 24 | SF | Sporting Kansas CitySporting Kans | 2 - 0 | Indy ElevenIndy Eleven |
| 29 Aug 24 | SF | Seattle Sounders FCSeattle Sound | 0 - 1 | Los Angeles FCLos Angeles F |
| |
| 26 Sep 24 | Final | Los Angeles FCLos Angeles F | 3 - 1 | Sporting Kansas CitySporting Kans |
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