| First Round | ||||
| Eastern Bracket | ||||
| 2/2/36 | Hatikvoh (NYC) | 1 : 2 | German Hungarian SC (NYC) | |
| 2/2/36 | Kearny Irish | 2 : 1 | Newark Germans | |
| 2/15/36 | Canton FC (Bal.) | 5 : 3 | Stonewall SC (Bal.) | |
| 3/1/36 | Kearny Scots | 2 : 0 | Trenton Highlanders | |
| 3/1/36 | German American SC (Phi.) | 5 : 0 | Budd AA (Phi.) | |
| 3/1/36 | Santo Christo (New Bedford, MA) | 2 : 1 | Liberal AC (Fall River) | |
| 3/1/36 | Brookhattan (NYC) | 3 : 3 | Brooklyn Hispano | |
| 3/8/36 | R | Brooklyn Hispano | 4 : 4 | Brookhattan |
| 3/15/36 | R | Brooklyn Hispano | 1 : 2 | Brookhattan |
| 3/7/36 | New York Americans | 2 : 3 | St. Mary’s Celtic (Brooklyn) | |
| Western Bracket | ||||
| 1/19/36 | Olympia SC (Chi.) | 3 : 2 | Maccabee SC (Chi.) | |
| 2/2/36 | Heidelberg (W. Pa.) | 4 : 0 | Curry Silver Tops (W. Pa.) | |
| 1/19/36 | Shamrocks SC (St. L) | 0 : 0 | Hellrung Grimm (St. L) | |
| 2/2/36 | R | Shamrocks SC | 6 : 1 | Hellrung Grimm |
| 1/19/36 | Bartunek Slavia (Cle.) | 2 : 1 | Highland Park Chrysler (Det.) | |
| 1/12/36 | Marres (St. L) | 4 : 2 | Burke Undertakers (St. L) | |
| 2/23/36 | Sparta Garden City (Chi.) | 6 : 0 | Ben Miller SC (St. L) | |
| 3/8/36 | Vienna AC (Mil.) | 5 : 4 | Bayern Schlitz (Mil.) | |
| 1/26/36 | Rochester Celtics | 0 : 4 |
Kodak Park (Roch.) | |
| Second Round | ||||
| Eastern Bracket | ||||
| 3/15/36 | German American SC | 3 : 2 | Canton FC | |
| 3/22/36 | Brookhattan | 2 : 0 | German Hungarian SC | |
| 3/22/36 | St. Mary’s Celtic | 4 : 1 | Santo Christo | |
| 3/22/36 | Kearny Scots | 2 : 0 | Kearny Irish | |
| Western Bracket | ||||
| 2/23/36 | Heidelberg | 4 : 1 | Kodak Park | |
| 3/1/36 | Sparta Garden City | 2 : 1 (aet) | Olympia SC | |
| 3/1/36 | Shamrocks SC | 4 : 3 | Bartunek Slavia | |
| 3/15/36 | Marres | 6 : 3 | Vienna AC | |
| Quarterfinals | ||||
| 3/22/36 | Shamrocks SC | 2 : 1 | Marres | |
| 3/22/36 | Sparta Garden City | 1 : 2 | Heidelburg | |
| 3/29/36 | St. Mary’s Celtic | 2 : 1 | Brookhattan | |
| 4/5/36 | Kearny Scots | 0 : 1 | German American SC | |
| Semifinals | ||||
| 4/12/36 | 1L | St. Mary’s Celtic | 0 : 2 | German American SC |
| 4/19/36 | 2L | German American SC | 0 : 1 | St. Mary’s Celtic |
| German American SC advance on 2-1 aggregate | ||||
| 3/29/36 | 1L | Shamrocks SC | 1 : 1 | Heidelburg SC |
| 4/5/36 | 2L | Heidelburg SC | 1 : 2 | Shamrocks SC |
| Shamrocks SC advance on 3-2 aggregate | ||||
| Final | ||||
| First Leg – at Walsh Memorial Stadium – St. Louis, Missouri | ||||
| 4/26/36 | Shamrocks SC | 2 : 2 | German American SC | |
| Second Leg – Rifle Club Grounds – Philadelphia, Pennsylvania | ||||
| 5/3/36 | German American SC | 3 : 0 | Shamrocks SC | |
| German American SC win National Challenge Cup on 5-2 aggregate | ||||
| KEY – w/o – Walkover, R – Replay, 1L – 1st Leg, 2L – 2nd Leg, 3L – 3rd Leg | ||||