| 12 Mar 23 |
r01        | San Diego LoyalSan Diego Loy | 1 - 0 | Detroit City FCDetroit City |
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| 19 Mar 23 |
r02        | El Paso LocomotiveEl Paso Locom | 1 - 3 | Detroit City FCDetroit City |
| 25 Mar 23 |
r02        | Detroit City FCDetroit City | 0 - 1 | Indy ElevenIndy Eleven |
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| |
| 02 Apr 23 |
r04        | Detroit City FCDetroit City | 0 - 1 | Rio Grande ValleyRio Grande Va |
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| |
| 08 Apr 23 |
r05        | Louisville CityLouisville Ci | 1 - 0 | Detroit City FCDetroit City |
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| |
| 16 Apr 23 |
r06        | Miami FCMiami FC | 0 - 0 | Detroit City FCDetroit City |
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| |
| 23 Apr 23 |
r08        | Sacramento RepublicSacramento Re | 1 - 0 | Detroit City FCDetroit City |
| 29 Apr 23 |
r08        | Detroit City FCDetroit City | 0 - 1 | Tampa Bay RowdiesTampa Bay Row |
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| |
| 07 May 23 |
r10        | Detroit City FCDetroit City | 1 - 1 | Tulsa RoughnecksTulsa Roughne |
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| |
| 14 May 23 |
r11        | Tampa Bay RowdiesTampa Bay Row | 5 - 1 | Detroit City FCDetroit City |
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| |
| 21 May 23 |
r13        | Detroit City FCDetroit City | 1 - 0 | San AntonioSan Antonio |
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| |
| 27 May 23 |
r14        | Detroit City FCDetroit City | 1 - 0 | Birmingham LegionBirmingham Le |
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| |
| 07 Jun 23 |
r16        | Charleston BatteryCharleston Ba | 0 - 0 | Detroit City FCDetroit City |
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| |
| 08 Jun 23 |
r15        | Charleston BatteryCharleston Ba | 0 - 0 | Detroit City FCDetroit City |
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| |
| 14 Jun 23 |
r17        | Hartford AthleticHartford Athl | 1 - 3 | Detroit City FCDetroit City |
| 18 Jun 23 |
r17        | Memphis 901Memphis 901 | 0 - 0 | Detroit City FCDetroit City |
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| |
| 25 Jun 23 |
r19        | Detroit City FCDetroit City | 0 - 1 | Orange County SCOrange County |
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| |
| 01 Jul 23 |
r20        | Tulsa RoughnecksTulsa Roughne | 3 - 2 | Detroit City FCDetroit City |
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| |
| 09 Jul 23 |
r22        | New Mexico UnitedNew Mexico Un | 1 - 0 | Detroit City FCDetroit City |
| 13 Jul 23 |
r22        | Detroit City FCDetroit City | 1 - 1 | Loudoun UnitedLoudoun Unite |
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| |
| 16 Jul 23 |
r23        | Pittsburgh RiverhoundsPittsburgh Ri | 2 - 0 | Detroit City FCDetroit City |
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| |
| 20 Jul 23 |
r24        | Detroit City FCDetroit City | 2 - 0 | Louisville CityLouisville Ci |
| 23 Jul 23 |
r24        | Detroit City FCDetroit City | 1 - 0 | Monterey Bay FCMonterey Bay |
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| |
| 30 Jul 23 |
r26        | Oakland RootsOakland Roots | 1 - 1 | Detroit City FCDetroit City |
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| |
| 13 Aug 23 |
r28        | Detroit City FCDetroit City | 0 - 1 | Charleston BatteryCharleston Ba |
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| |
| 20 Aug 23 |
r29        | Detroit City FCDetroit City | 1 - 0 | Las Vegas LightsLas Vegas Lig |
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| |
| 27 Aug 23 |
r32        | Birmingham LegionBirmingham Le | 2 - 3 | Detroit City FCDetroit City |
| 03 Sep 23 |
r32        | Detroit City FCDetroit City | 1 - 1 | Memphis 901Memphis 901 |
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| 10 Sep 23 |
r34        | Detroit City FCDetroit City | 2 - 1 | Miami FCMiami FC |
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| |
| 17 Sep 23 |
r35        | Phoenix RisingPhoenix Risin | 5 - 0 | Detroit City FCDetroit City |
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| |
| 24 Sep 23 |
r36        | Detroit City FCDetroit City | 3 - 0 | Hartford AthleticHartford Athl |
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| |
| 28 Sep 23 |
r37        | Detroit City FCDetroit City | 0 - 3 | Colorado SpringsColorado Spri |
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| |
| 01 Oct 23 |
r38        | Indy ElevenIndy Eleven | 3 - 0 | Detroit City FCDetroit City |
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| |
| 07 Oct 23 |
r39        | Loudoun UnitedLoudoun Unite | 0 - 3 | Detroit City FCDetroit City |
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| |
| 14 Oct 23 |
r40        | Detroit City FCDetroit City | 0 - 0 | Pittsburgh RiverhoundsPittsburgh Ri |
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| |
| 22 Oct 23 |
r16        | Pittsburgh RiverhoundsPittsburgh Ri | 0 - 1 | Detroit City FCDetroit City |
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| |
| 28 Oct 23 |
QF        | Louisville CityLouisville Ci | 2 - 0 | Detroit City FCDetroit City |
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| 29 Oct 23 |
r00        | Louisville CityLouisville Ci | 4 - 0 | Detroit City FCDetroit City |