| First Round | ||||
| Eastern Bracket | ||||
| 1/16/38 | Kearny Irish | 3 : 5 | Bethlehem Hungarian | |
| 1/16/38 | New York Americans | 4 : 2 | Brooklyn First Germans | |
| 1/16/38 | Brooklyn Hispano | 1 : 1 (aet) | St. Mary’s Celtic (Brooklyn) | |
| 1/22/38 | R | St. Mary’s Celtic | 4 : 1 | Brooklyn Hispano |
| 1/16/38 | Paterson Caledonians | 1: 0 | Kearny Scots | |
| 1/16/38 | Baltimore SC | 2 : 1 | Budd AA (Phi.) | |
| 1/16/38 | German American SC (Phi.) | 3 : 3 | Passon SC (Phi.) | |
| 1/23/38 | R | German American SC | 2 : 0 | Passon SC |
| 1/23/38 | Brookhattan (NYC) | 4 : 1 | Hatikvoh (NYC) | |
| 1/30/38 | Lusitania Recriation | 3 : 3 | Ponta Delgada | |
| Western Bracket | ||||
| 1/16/38 | Maccabee SC (Chi.) | 2 : 0 (aet) | American Nickeloid (Peru, IL) | |
| 1/16/38 | Schlitz (Mil.) | 6 : 4 | Racine Deutscher (WI) | |
| 1/16/38 | Castle Shannon (W. Pa.) | 2 : 0 | Heidelberg (W. Pa.) | |
| 1/16/38 | South Side Radio (St. L) | 3 : 2 | St. Patricks (St. L) | |
| 1/16/38 | Sparta Garden City (Chi.) | w/o | Shamrocks SC (St. L) | |
| 1/23/38 | Bartunek Slavia (Cle.) | 3 : 1 | Cecil Merchants (W. Pa.) | |
| 1/30/38 | Burke Undertakers (St. L) | 5 : 4 | St. Matthews (St. L) | |
| 2/13/38 | Thistles SC (Det.) | 5 : 1 | Eckert & Becker (Det.) | |
| Second Round | ||||
| Eastern Bracket | ||||
| 1/30/38 | New York Americans | 4 : 1 | Bethlehem Hungarian | |
| 1/30/38 | St. Mary’s Celtic | 7 : 1 | Baltimore SC | |
| 1/30/38 | German American SC | 5 : 3 | Paterson Caledonian | |
| 2/20/38 | Brookhattan | 7 : 0 | Ponta Delgada | |
| Western Bracket | ||||
| 1/30/38 | Maccabee SC | 2 : 1 | Schlitz | |
| 1/30/39 | Castle Shannon | 3 : 0 | Bartunek Slavia | |
| 2/6/38 | South Side Radio | 1 : 0 | Burke Undertakers | |
| 2/20/38 | Sparta Garden City | 5 : 0 | Thistles SC | |
| Quarterfinals | ||||
| 2/20/38 | Castle Shannon | 4 : 2 | South Side Radio | |
| 2/27/38 | New York Americans | 4 : 3 | Brookhattan | |
| 2/27/38 | St. Mary’s Celtic | 1 : 1 (aet) | German American SC | |
| 3/5/38 | R | St. Mary’s Celtic | 1 : 0 | German American SC |
| 2/27/38 | Sparta Garden City | 1 : 0 | Maccabee SC | |
| Semifinals | ||||
| 3/27/38 | 1L | New York Americans | 2 : 1 | St. Mary’s Celtic |
| 4/2/38 | 2L | St. Mary’s Celtic | 3 : 0 | New York Americans |
| St. Mary’s Celtic advance on 4-2 aggregate | ||||
| 3/13/38 | 1L | Castle Shannon | 1 : 2 | Sparta Garden City |
| 3/20/38 | 2L | Sparta Garden City | 3 : 1 | Castle Shannon |
| Sparta Garden City advance on 5-2 aggregate | ||||
| Final | ||||
| First Leg – at Sparta Stadium – Chicago, Illinois | ||||
| 4/17/38 | Sparta Garden City | 3 : 0 | St. Mary’s Celtic | |
| Second Leg – at Starlight Park – Bronx, New York | ||||
| 4/24/38 | St. Mary’s Celtic | 2 : 3 | Sparta Garden City | |
| Sparta Garden City win National Challenge Cup on 6-2 aggregate | ||||
| KEY – w/o – Walkover, R – Replay, 1L – 1st Leg, 2L – 2nd Leg, 3L – 3rd Leg | ||||
Castle Shannon
1937 National Challenge Cup Results
| First Round | ||||
| Eastern Bracket | ||||
| 1/10/37 | Kearny Scots | 4 : 1 (aet) | Patapsco Rangers (Bal.) | |
| 1/17/37 | Kearny Irish | 3 : 1 | St. Michael’s | |
| 1/17/37 | New York Americans | 4 : 0* | German Hungarian SC (NYC) | |
| *Match abandoned at 60th minute due to heavy rain | ||||
| 2/7/37 | R | New York Americans | 6 : 2 | German Hungarian SC |
| 1/17/37 | Brooklyn Hispano | 6 : 0 | Hosiery Local (Phi.) | |
| 1/17/37 | Passon SC (Phi.) | 4 : 0 | Haitkvoh (NYC) | |
| 1/24/37 | Brookhattan (NYC) | 5 : 1 | Baltimore SC | |
| 1/24/37 | Philadelphia Germans | 5 : 2 (aet) | Trenton Highlanders | |
| 1/24/37 | St. Mary’s Celtic (Brooklyn) | 5 : 1 | Paterson Caledonian | |
| Western Bracket | ||||
| 1/10/37 | Kodak Park (Roch.) | 0 : 2 | Heidelberg (W. Pa.) | |
| 1/10/37 | Pittsburgh Steel | 0 : 1 | Castle Shannon (W. Pa.) | |
| 1/10/37 | Chevrolet SC (Det.) | 0 : 4 | Shamrocks SC (St. L) | |
| 1/10/37 | Olympia SC (Chi.) | 2 : 1 | Maccabee SC (Chi.) | |
| 1/18/37 | Sparta Garden City (Chi.) | 3 : 1 (aet) | Vienna AC (Mil.) | |
| 1/31/37 | Bartunek Slavia (Cle.) | 3 : 2 | Graphite Bronze (Cle.) | |
| 2/7/37 | Town Criers (St. L) | 5 : 1 | Club Lotus (St. L) | |
| 2/14/37 | Burke Undertakers (St. L) | 1 : 0 | North Side Optimists (St. L) | |
| Second Round | ||||
| Eastern Bracket | ||||
| 2/7/37 | Brooklyn Hispano | 3 : 2 | Brookhattan | |
| 2/7/37 | Kearny Scots | 2 : 1 | Passon SC | |
| 2/7/37 | German American SC | 1 : 1 (aet) | Kearny Irish | |
| 2/14/37 | R | Kearny Irish | 1 : 0 | German American SC |
| 2/21/37 | New York Americans | 2 : 1 | St. Mary’s Celtic | |
| Western Bracket | ||||
| 1/31/37 | Sparta Garden City | 5 : 0 | Olympia SC | |
| 2/7/37 | Shamrocks SC | 1 : 0 | Bartunek Slavia | |
| 1/31/37 | Castle Shannon | 2 : 1 | Heidelberg | |
| 2/28/37 | Town Criers | 2 : 1 | Burke Undertakers | |
| Quarterfinals | ||||
| 3/7/37 | Shamrocks SC | 2 : 1 | Town Criers | |
| 2/21/36 | Sparta Garden City | 6 : 4 | Castle Shannon | |
| 2/28/37 | Kearny Irish | 0 : 1 | Brooklyn Hispano | |
| 3/28/37 | New York Americans | 2 : 1 | Kearny Scots | |
| Semifinals | ||||
| 3/13/37 | 1L | Brooklyn Hispano | 2 : 0 | New York Americans |
| 3/14/37 | 2L | New York Americans | 3 : 0 | Brooklyn Hispano |
| New York Americans advance on 3-2 aggregate | ||||
| 3/21/37 | 1L | Shamrocks SC | 3 : 1 | Sparta Garden City |
| 4/4/37 | 2L | Sparta Garden City | 0 : 0 | Shamrocks SC |
| Shamrocks SC advance on 3-1 aggregate | ||||
| Final | ||||
| First Leg – at St. Louis, Missouri | ||||
| 4/11/37 | Shamrocks SC | 1 : 0 | New York Americans | |
| Second Leg – Starlight Park – Bronx, New York | ||||
| 4/18/37 | New York Americans | 4 : 2 | Shamrocks SC | |
| New York Americans win National Challenge Cup on 4-3 aggregate | ||||
| KEY – w/o – Walkover, R – Replay, 1L – 1st Leg, 2L – 2nd Leg, 3L – 3rd Leg | ||||