| First Round | ||||
| Eastern Bracket | ||||
| 11/5/39 | Lusitania Recreation | 3 : 1 | Ludlow Lusitano | |
| 11/5/39 | St. Michaels (Mass.) | 2 : 0* | Newark Portuguese | |
| *Match abandoned after 35 minutes due to heavy rain | ||||
| 11/12/39 | R | St. Michaels | 2 : 1 | Newark Portuguese |
| 11/12/39 | Baltimore SC | 10 : 1 | St. Gerard (Bal.) | |
| 11/12/39 | German American SC (Phi.) | 4 : 0 | German SC (Reading) | |
| 11/12/39 | New York Americans | 3 : 0 | German Hungarian SC | |
| 11/12/39 | Swedish FC (NYC) | 2 : 1 | Haitkvoh (NYC) | |
| 11/12/39 | Kearny Scots | 9 : 0 | Allentown SC | |
| 11/12/39 | St. Mary’s Celtic (Brooklyn) | 2 : 0 | Brooklyn Hispano | |
| 11/12/39 | Gjoa SC (NYC) | 3 : 1 | German S.C. (Brooklyn) | |
| 11/12/39 | Norwegian American SC (NYC) | 2 : 1 | Kollsman (NYC) | |
| 11/18/39 | Holy Cross | 0 : 2 | Pawtucket FC | |
| 11/19/39 | Brookhattan | 3 : 0 | Galicia (NYC) | |
| 11/19/39 | Firestone FC (Mass.) | W : L | Baylies (Mass.) | |
| 11/19/39 | Paterson SC (NJ) | 4 : 0 | Kearny Irish | |
| 11/19/39 | Passon SC (Phi.) | 1 : 0 | German SC (Phi.) | |
| 11/19/39 | Baltimore Americans | 2 : 4 (aet) | Kensington Blue Bells (Phi.) | |
| Western Bracket | ||||
| 11/5/39 | Viking A.A. (Chi.) | 1 : 1 | Swedish American SC (Chi.) | |
| 11/12/39 | R | Viking A.A. | 1 : 3 | Swedish American SC |
| 11/5/39 | Sparta Fallstaff (Chi.) | 4 : 0 | Olympia SC (Chi.) | |
| 11/5/39 | Shamrocks SC (Cle.) | 3 : 1 | Dalarda SC (Cle.) | |
| 11/12/39 | Bartunek Clothes (Cle.) | 7 : 2 | Dunlevy (W. Pa.) | |
| 11/5/39 | Hungarian Sports Club (Mil.) | 3 : 3 | Schlitz (Mil.) | |
| 11/12/39 | R | Hungarian Sports Club | 5 : 4 | Schlitz |
| 11/5/39 | Morgan Sport Club (W. Pa.) | 1 : 0 | Cuddy (W. Pa.) | |
| 11/5/39 | Harmarville (W. Pa.) | 1 : 6 | Heidelberg (W. Pa.) | |
| 11/5/39 | Glendale (W. Pa.) | 3 : 0 | Muse (W. Pa.) | |
| 11/5/39 | Canonsburg (W. Pa.) | 2 : 0 | Gallatin (W. Pa.) | |
| 11/5/39 | Curry (W. Pa.) | 2 : 4 | Castle Shannon (W. Pa.) | |
| 11/5/39 | Buffalo City Hungarian SC | 3 : 1 | MacKenzie SC (Niagra Falls) | |
| 11/5/39 | Becks German American SC (Buf.) | 9 : 5 (aet) | German AC (Roch.) | |
| Manhattan Beer (Chi.) | bye | |||
| Chrysler SC (Det.) | bye | |||
| Celtic SC (Det.) | bye | |||
| Thistles SC (Roch.) | bye | |||
| Second Round | ||||
| Eastern Bracket | ||||
| 12/3/39 | Brookhattan | 2 : 1 | Swedish FC | |
| 12/3/39 | Kearny Scots | 3 : 2 | Paterson SC | |
| 12/4/39 | Baltimore SC | 5 : 1 | Kensington Blue Bells | |
| 12/10/39 | New York Americans | 1 : 0 | Gjoa SC | |
| 12/10/39 | German American SC | 2 : 2 | Passon SC | |
| 12/16/39 | R | German American SC | 4 : 2 (aet) | Passon SC |
| 12/3/39 | Lusitania Recreation | 4 : 1 | Pawtucket FC | |
| 12/4/39 | St. Mary’s Celtic | 1 : 0 | Norwegian American SC | |
| 12/10/39 | Firestone FC | 3 : 0 | St. Michaels | |
| Western Bracket | ||||
| 12/3/39 | Sparta Fallstaff | 2 : 0 | Manhattan Beer | |
| 12/3/39 | Swedish American SC | 7 : 0 | Hungarian Sports Club | |
| 12/3/39 | Thistles SC | 1 : 6 | Canonsburg | |
| 12/3/39 | Heidelberg | 2 : 1 | Castle Shannon | |
| 12/10/39 | Morgan Sport Club | 3 : 3 (aet) | Glendale | |
| 12/17/39 | R | Morgan Sport Club | 0 : 0(aet) | Glendale |
| 12/25/39 | R | Morgan Sport Club | 2 : 0* | Glendale |
| *Match abandoned at 70th minute due to crowd trouble | ||||
| 12/31/39 | R | Morgan Sport Club | 5 : 0 | Glendale |
| 12/10/39 | Buffalo Becks | 4 : 2 | Buffalo City Hungarian SC | |
| 12/10/39 | Chrysler SC | 3 : 1 | Celtic SC | |
| 12/24/39 | Bartunek Slavia | 0 : 2 | Shamrocks SC | |
| Third Round | ||||
| Eastern Bracket | ||||
| 1/1/40 | German American SC | 1 : 4 | Baltimore SC | |
| 1/1/40 | Kearny Scots | 3 : 4(aet) | St. Mary’s Celtic | |
| 1/1/40 | Brookhattan | 1 : 1 | New York Americans | |
| 1/21/40 | R | Brookhattan | 1 : 0 | New York Americans |
| 1/1/40 | Lusitania Recreation | 2 : 2 | Firestone FC | |
| 1/6/40 | R | Lusitania Recreation | 5 : 2 | Firestone FC |
| Western Bracket | ||||
| 12/17/39 | Sparta Falstaff | 2 : 0 | Swedish American SC | |
| 12/24/39 | Chrysler SC | 3 : 0 | Shamrocks SC | |
| 1/14/40 | Morgan Sport Club | 8 : 1 | Buffalo Becks | |
| 1/1/40 | Heidelberg | W : L | Cannonsburg | |
| Quarterfinals | ||||
| 3/17/40 | St. Mary’s Celtic | 2 : 3 | Baltimore SC | |
| 3/17/40 | Lusitania Recreation | 2 : 2 | Brookhattan | |
| 3/17/40 | Sparta Fallstaff | 1 : 0 | Chrysler SC | |
| 3/17/40 | Morgan Sport Club | 2 : 0 | Heidelburg SC | |
| Semifinals | ||||
| 4/13/40 | 1L | Baltimore SC | 3 : 1 | Brookhattan |
| 4/15/40 | 2L | Brookhattan | 2 : 2 | Baltimore SC |
| Baltimore SC advance on 5-3 aggregate | ||||
| 4/7/40 | 1L | Spatra Fallstaff | 1 : 1 | Morgan Sport Club |
| 4/14/40 | 2L | Morgan Sport Club | 1 : 1 (aet) | Sparta Fallstaff |
| 4/21/40 | R | Sparta Fallstaff | 1 : 0 | Morgan Sport Club |
| Sparta Fallstaff advance on 3-2 aggregate | ||||
| Final | ||||
| First Leg – at Bugle Field – Baltimore, Maryland | ||||
| 5/5/40 | Baltimore SC | 0 : 0 | Sparta Fallstaff | |
| Second Leg – at Sparta Stadium – Chicago, Illinois | ||||
| 5/12/40 | Sparta Fallstaff | 2 : 2(aet) | Baltimore SC | |
| Aggregate drawn 2-2, Championship shared when details for a third game could not be agreed upon | ||||
| KEY – w/o – Walkover, R – Replay, 1L – 1st Leg, 2L – 2nd Leg, 3L – 3rd Leg | ||||
Lusitania Recreation
1939 National Challenge Cup Results
| Round of 32 | ||||
| Eastern Bracket | ||||
| 1/9/39 | Baltimore SC | 4 : 0 | Brooklyn Hakoah | |
| 1/9/39 | Brooklyn Hispano | 1 : 2 | Holy Cross (Fall River) | |
| 1/9/39 | Brookhattan (NYC) | 4 : 1 | Bethlehem Hungarian SC | |
| 1/9/39 | German American SC (Phi.) | 2 : 1 | Baltimore German SC | |
| 1/9/39 | Trenton Highlanders | 2 : 0 | Kearny Irish | |
| 1/29/39 | New York Americans | 1 : 3 | St. Mary’s Celtic (Brooklyn) | |
| 2/5/39 | Passon SC (Phi.) | 3 : 3 | Kearny Scots | |
| 2/10/39 | R | Kearny Scots | 3 : 2 | Passon SC (Phi.) |
| 1/8/39 |
Lusitania Recreation | 4 : 3 |
St. Michael’s | |
| 1/22/39 | Lusitania Recreation | 1 : 0 | St. Michael’s | |
| Western Bracket | ||||
| 12/11/38 | Sparta Garden City (Chi.) | 1 : 0 | Olympia SC (Chi.) | |
| 12/11/38 | Manahttan Beer (Chi.) | 4 : 0 | Swedish American SC (Chi.) | |
| 12/11/38 | German Sport Club (W. Pa.) | 3 : 0 | Curry (W. Pa) | |
| 12/11/38 | Morgan Sports Club (Pit.) | 2 : 1 | Heidelberg (W. Pa.) | |
| 12/11/378 | Shamrock SC (Cle.) | 2 : 2 | Bartunek Slavia (Cle.) | |
| 12/18/38 | R | Shamrock SC | 0 : 0 (aet) | Bartunek Slavia |
| 1/2/39 | R | Shamrock SC | 1 : 5 | Bartunek Slavia |
| Kodak Park (Roch.) | ||||
| 12/11/38 |
Lindell Trust (St. L) | 3 : 1 |
Burke(St. L) | |
| Chrysler SC (Det.) | ||||
| Round of 16 | ||||
| Eastern Bracket | ||||
| 2/12/39 | German American SC | 1 : 0 | Baltimore SC | |
| 2/12/39 | St. Mary’s Celtic | 6 : 4 (aet) | Trenton Highlanders | |
| 3/19/39 | Brookhattan | 1 : 0 | Kearny Scots | |
| 2/12/39 |
Lusitania Recreation | 1 : 1 |
Holy Cross | |
| 2/19/39 |
Lusitania Recreation | 2 : 1 |
Holy Cross | |
| Western Bracket | ||||
| 1/8/39 | Sparta Garden City | 7 : 1 | Lindell Trust | |
| 1/8/39 | Manhattan Beer | 4 : 2 | Chrysler SC | |
| 1/8/39 | German Sport Club | 1 : 1 (aet) | Morgan Sport Club | |
| 1/15/39 |
R | Morgan Sport Club | 5 : 0 | German Sport Club |
| 1/8/39 | Kodak Park | 1 : 1 (aet) | Bartunek Slavia | |
| 1/15/39 | R | Bartunek Slavia | 3 : 0 | Kodak Park |
| Quarterfinals | ||||
| 3/12/39 | Manhattan Beer | 3 : 2 | Bartunek Slavia | |
| 3/12/39 | Morgan Sport Club | 4 : 2 | Sparta A & BA | |
| 3/26/39 | German American SC | 3 : 2 (aet) | Lusitania Recreation | |
| 4/2/39 | Brookhattan | 1 : 3 | St. Mary’s Celtic | |
| Semifinals | ||||
| 4/15/39 | 1L | German American SC | 0 : 2 | St. Mary’s Celtic |
| 4/16/39 | 2L | St. Mary’s Celtic | 1 : 2 | German American SC |
| St. Mary’s Celtic advance on 3-2 aggregate | ||||
| 4/2/39 | 1L | Morgan Sport Club | 3 : 2 | Manhattan Beer |
| 4/19/39 | 2L | Manhattan Beer | 3 : 1 | Morgan Sport Club |
| Manhattan Beer advance on 5-4 aggregate | ||||
| Final | ||||
| First Leg – at Sparta Stadium – Chicago, Illinois | ||||
| 4/30/39 | Manhattan Beer | 0 : 1 | St. Mary’s Celtic | |
| Second Leg – Starlight Park – Bronx, New York | ||||
| 5/7/39 | St. Mary’s Celtic | 4 : 1 | Manhattan Beer | |
| St. Mary’s Celtic win National Challenge Cup on 5-2 aggregate | ||||
| KEY – w/o – Walkover, R – Replay, 1L – 1st Leg, 2L – 2nd Leg, 3L – 3rd Leg | ||||