| First Round | |||||
| Eastern Bracket | |||||
| 1/26/30 | New Bedford Whalers | 4 : 0 | Bridgeport Hungaria | ||
| 2/2/30 | New York Giants | 6 : 0 | New York Hispano | ||
| 2/2/30 | Brooklyn Wanderers | 6 : 0 | Monclair Camerons | ||
| 2/2/30 | Hakoah All Stars | 3 : 1 | I.R.T. Rangers | ||
| 2/2/30 | Fall River Marksmen | 5 : 0 | Lusitania Recreation | ||
| 2/2/30 | Pawtucket Rangers | 3 : 1 | Providence Gold Bugs | ||
| 2/9/30 | Newark Portuguese | 1 : 8 | Bethlehem Steel | ||
| New York Nationals receive a bye | |||||
| (Nationals were shown drawn against Newark in the 1/8/30 New York Times. Newark apparently withdrew) | |||||
| Western Bracket | |||||
| 12/25/29 | Sparta FC (Chi.) | 9 : 3 | Olympia SC (Chi.) | ||
| 12/29/29 | Madison Kennel SC (St. L) | 1 : 3 | Hellrungs FC (St. L) | ||
| 12/29/29 | Swedish American FC (Chi.) | 1 : 1(aet) | Bricklayers FC (Chi.) | ||
| 1/5/30 | R | Swedish American FC | 1 : 2(aet) | Bricklayers FC | |
| 12/29/29 | Bruell Insurance (Cle.) | 5 : 5 | Bartunek Slavia (Cle.) | ||
| 1/5/30 | R | Bruell Insurance | 0 : 0(aet) | Bartunek Slavia | |
| 1/12/30 | R | Bruell Insurance | 3 : 2(aet) | Bartunek Slavia | |
| 12/29/29 | Carpenters FC (Chi.) | 2 : 2 | Yugoslav American SC (Chi.) | ||
| 1/5/30 | R | Carpenters FC | 2 : 2 | Yugoslav American SC | |
| 1/5/30 | Ben Miller SC (St. L) | 2 : 4 | Tablers FC (St. L) | ||
| 2/3/30 | Holley Carburetor (Det.) | 6 : 1 | Pierpoints FC (Pit.) | ||
| 2/10/30 | Detroit FC | 3 : 3 | All Scots FC (Det.) | ||
| 2/17/30 | R | Detroit FC | 1 : 0 | All Scots FC | |
| Second Round | |||||
| Eastern Bracket | |||||
| 2/15/30 | Pawtucket Rangers | 3 : 2 | New York Nationals | ||
| 2/16/30 | Brooklyn Wanderers | 2 : 1 | Hakoah All Stars | ||
| 2/23/30 | New York Giants | 1 : 2 | Bethlehem Steel | ||
| 2/22/30 | Fall River Marksmen | 5 : 2 | New Bedford Whalers | ||
| Western Bracket | |||||
| 2/16/30 | Bruell Insurance | 2 : 0 | Sparta FC | ||
| 2/23/30 | Detroit FC | 1 : 3 | Holley Carburetor | ||
| 2/23/30 | Tablers FC | 3 : 2 | Hellrungs FC | ||
| 2/23/30 | Bricklayers FC | 1 : 1 | Carpenters FC | ||
| 3/2/30 | R | Bricklayers FC | 3 : 0 | Carpenters FC | |
| Quarterfinals | |||||
| 3/2/30 | Brooklyn Wanderers | 0 : 2 | Bethlehem Steel | ||
| 3/2/30 | Fall River Marksmen | 5 : 2 | Pawtucket Rangers | ||
| 3/3/30 | Tablers FC | 1 : 3 | Bruell Insurance | ||
| 3/9/30 | Bricklayers FC | 1 : 2 | Holley Carburetor | ||
| Semifinals | |||||
| 3/16/30 | Bethlehem Steel | 1 : 1 | Fall River Marksmen | ||
| 3/23/30 | R | Fall River Marksmen | 3 : 2 | Bethlehem Steel | |
| 3/23/30 | Bruell Insurance | 2 : 0 | Holley Carburetor | ||
| Final | |||||
| First Leg – at Polo Grounds – New York, New York | |||||
| 3/30/30 | Fall River Marksmen | 7 : 2 | Bruell Insurance | ||
| Second Leg – at Luna Park – Cleveland, Ohio | |||||
| 4/6/30 | Bruell Insurance | 1 : 2 | Fall River Marksmen | ||
| Fall River Marksmen win National Challenge Cup on 9-3 aggregate | |||||
| KEY – w/o – Walkover, R – Replay | |||||
Brooklyn Wanderers
1928 National Challenge Cup Results
| First Round | ||||
| *advanced from qualifying rounds. All other clubs exempt from qualifying | ||||
| Eastern Bracket | ||||
| 1/14/28 | Boston Wonder Workers | 3 : 0 | Whittall Carpet Mills | |
| 1/14/28 | New Bedford Whalers | 2 : 1 | J & P Coats | |
| 1/15/28 | New York Nationals | 6 : 1 | I.R.T. Celtics (NYC)* | |
| 1/15/28 | Bethlehem Steel | 3 : 1 | Centennial FC (Phi.)* | |
| 1/15/28 | Brooklyn Wanderers | 4 : 0 | Trenton FC | |
| 1/15/28 | Fall River Marksmen | 5 : 1 | MacKenzie FC (Niagara Falls)* | |
| 1/15/28 | New York Giants | 3 : 2 | Newark Skeeters | |
| 1/15/28 | Providence Clamdiggers | 5 : 0 | Danersk FC (CT) | |
| Western Bracket | ||||
| 1/15/28 | Magyar American FC (Cle.)* | 2 : 1 | Wellston FC (St. L) | |
| 1/15/28 | Gar Wood FC (Det.)* | 2 : 5 | Bricklayers FC (Chi.) | |
| 1/15/28 | Morgan Haulers (St. L) | 3 : 6 | Buda A.A. (Harvey, Ill.)* | |
| 1/15/28 | Canadian Club (Chi.) | 4 : 1 | Tablers FC (St. L) | |
| 1/22/28 | Ben Miller SC (St. L) | 2 : 0 | Swedish American FC (Det.) | |
| 1/22/28 | Walkerville (Ont.)* | 0 : 5 | Holley Carburetor (Det.) | |
| 1/23/28 | Vienna FC (Chi.) | 1 : 0 | Thistle FC (Chi.) | |
| 1/22/28 |
Sparta A & BA (Chi.) | 2 : 0 | Olympia FC (Chi.) | |
| Second Round | ||||
| Eastern Bracket | ||||
| 1/28/28 | J & P Coats | 1 : 0 | Providence Clamdiggers | |
| 1/29/28 | Fall River Marksmen | 2 : 1 | Boston Wonder Workers | |
| 1/29/28 | Brooklyn Wanderers | 1 : 1 (aet) | Bethlehem Steel | |
| 2/4/28 | R | Brooklyn Wanderers | 3 : 2 (aet) | Bethlehem Steel |
| 2/5/28 | New York Nationals | 2 : 2 (aet) | New York Giants | |
| 2/12/28 | R | New York Giants | 1 : 2 | New York Nationals |
| Western Bracket | ||||
| 2/5/28 | Ben Miller SC | 2 : 1 | Canadian Club | |
| 2/5/28 | Bricklayers FC | 4 : 0 | Buda A.A. | |
| 2/5/28 | Magyar American FC | 5 : 2 | Vienna FC | |
| 2/5/28 | Holley Carburetor | 3 : 4 (aet) | Sparta A & BA | |
| Quarterfinals | ||||
| 2/26/28 | Brooklyn Wanderers | 0 : 1 | New York Nationals | |
| 2/26/28 | J & P Coats | 2 : 1 | Fall River Marksmen | |
| 2/26/28 | Ben Miller FC | 4 : 3 (aet) | Magyar American FC | |
| 2/26/28 | Bricklayers FC | 1 : 0 | Sparta A & BA | |
| Semifinals | ||||
| 3/18/18 | New York Nationals | 5 : 3 | J & P Coats | |
| 3/18/28 | Ben Miller FC | 0 : 2 | Bricklayers FC | |
| Final | ||||
| at Polo Grounds, New York, New York | ||||
| 4/9/28 | New York Nationals | 1 : 1(aet) | Bricklayers FC | |
| at Soldier Field, Chicago, Illinois | ||||
| 4/15/28 | R | New York Nationals | 3 : 0 | Bricklayers FC |
| KEY – w/o – Walkover, R – Replay | ||||
1946 National Challenge Cup Results
| Round of 32 | ||||
| Eastern Bracket | ||||
| 2/10/46 | Brooklyn Wanderers | 2: 1 | German Hungarian SC (NYC) | |
| 3/10/46 | Brooklyn Hispano | 3 : 0 | Hakoah SC (NYC) | |
| 3/17/46 | Baltimore SC | 4 : 2 | Ruggiero SC (Bal.) | |
| 3/17/46 | Baltimore Americans | 6 : 1 | Hasslinger SC (Bal.) | |
| 4/21/46 | New York Americans | 5 : 1 | Eintracht SC (NYC) | |
| 4/21/46 | Kearny Americans | 1 : 0 | Elizabeth SC | |
| Ponta Delgada | ||||
| Philadelphia Americans | ||||
| Western Bracket | ||||
| 1/6/46 | Castle Shannon (W. Pa.) | 4 : 3 | Morgan Strasser (W. Pa.) | |
| 1/13/46 | Heidelberg Losegos (W. Pa.) | 2 : 1 | Sturgeon (W. Pa.) | |
| Replay ordered after Sturgeon protest was upheld | ||||
| 1/27/46 | R | Heidelberg Losegos | 9 : 1 | Sturgeon |
| 3/17/46 | Cleveland Americans | 7 : 1 | Becks German American SC (Buf.) | |
| 3/24/46 | Sparta (Chi.) | 7 : 1 | Schlitz SC (Mil.) | |
| 3/24/46 | Viking AA (Chi.) | 6 : 2 | Necaxa (Chi.) | |
| Pioneer Kickers (Det.) | ||||
| Carondelet (St. L) | ||||
| 2/10/46 |
Raferty Painters (St. L) | 2 : 1 |
Natural Set Ups | |
| Round of 16 | ||||
| Eastern Bracket | ||||
| 4/28/46 | 1L | Ponta Delgada | 2 : 0 | New York Americans |
| 5/5/46 | 2L | New York Americans | 2 : 3 | Ponta Delgada |
| Ponta Delgada advance on 5-2 aggregate | ||||
| 5/5/46 | Brooklyn Wanderers | 3 : 0 | Brooklyn Hispanos | |
| 5/5/46 | Baltimore Americans | w/o | Baltimore SC | |
| 4/28/46 | 1L | Philadelphia Americans | 1 : 0 | Kearny Scots |
| 5/5/46 | 2L | Philadelphia Americans | 2 : 2 | Kearny Scots |
| Philadelphia Americans advance on 3-2 aggregate | ||||
| Western Bracket | ||||
| 2/10/46 | Heidelberg Losegos | 1 : 0 | Castle Shannon | |
| 3/31/46 | Viking AA | 2 : 1 (aet) | Sparta | |
| 4/13/46 |
Carondelet | 4 : 2 |
Raferty | |
| 4/14/46 | Cleveland Americans | 0 : 0 (aet) | Pioneer Kickers | |
| 4/21/46 | R | Cleveland Americans | 2 : 1 (aet) | Pioneer Kickers |
| Quarterfinals | ||||
| 4/28/46 | Viking A.A. | 1 : 0 | Carondolet | |
| 5/26/46 | 1L | Brooklyn Wanderers | 1 : 2* | Ponta Delgada |
| *Match protested by Brooklyn over a shortage of eight minutes playing time in the first half. | ||||
| Match replayed after second leg. | ||||
| 6/3/46 | 2L | Ponta Delgada | 1 : 1 | Brooklyn Wanderers |
| 6/17/46 | 1LR | Brooklyn Wanderers | 1 : 3 | Ponta Delgada |
| Ponta Delgada advance on 4-2 aggregate | ||||
| 6/10/46 | Philadelphia Americans | 4 : 2 |
Baltimore Americans | |
| 4/28/46 | Heidelberg Losegos | 2 : 1 (aet) | Cleveland Americans | |
| Semifinals | ||||
| 6/23/46 | 1L | Ponta Delgada | 4 : 2 | Philadelphia Americans |
| 6/30/46 | 2L | Philadelphia Americans | 3 : 2 | Ponta Delgada |
| Ponta Delgada advance on 6-5 aggregate | ||||
| 5/12/46 | 1L | Heidelberg S.C. | 3 : 1 | Viking A.A. |
| 5/20/46 | 2L | Viking A.A. | 2 : 0(aet) | Heidelberg S.C. |
| 5/27/46 | 3L | Viking A.A. | 3 : 1 | Heidelberg S.C. |
| Viking AA advance on 6-4 aggregate | ||||
| Final | ||||
| First Leg – at Mark’s Stadium – Tiverton, Rhode Island | ||||
| 7/7/46 | Ponta Delgada | 1 : 1 | Viking A.A. | |
| Second Leg – at Comiskey Park – Chicago, Illinois | ||||
| 7/14/46 | Viking A.A. | 2 : 1 | Ponta Delgada | |
| Viking AA win National Challenge Cup on 3-2 aggregate | ||||
| KEY – w/o – Walkover, R – Replay, 1L – 1st Leg, 2L – 2nd Leg, 3L – 3rd Leg | ||||
1943 National Challenge Cup Results
| Round of 32 | ||||
| Eastern Bracket | ||||
| 1/3/43 | Philadelphia Americans | 1 : 0 | Baltimore Americans | |
| 1/3/43 | Brookhattan (NYC) | 7 : 2 | Fall River Rovers | |
| 1/3/43 | Kearny Scots | 3 : 1 | Pfaelzer (NYC) | |
| 1/10/43 | New York Americans | 2 : 1 | New York Germans | |
| 1/10/43 | Brooklyn Hispano | 3 : 0 | German Hungarian S.C. (NYC) | |
| 1/10/43 | Kearny Celtic | 3 : 0 | Eintracht (NYC) | |
| Philadelphia Nationals | ||||
| 1/3/43 | Brooklyn Wanderers | 1 : 0 | Swedish SC (NYC) | |
| Eastern Bracket | ||||
| 1/11/43 | Sparta SC (Chi.) | 3 : 1 | Schwaben (Chi.) | |
| 2/21/43 | Slovak SC (Chi.) | 2: 1 (aet) | Viking AA (Chi.) | |
| 4/4/43 | Falk Field Club (Mil.) | 4 : 1 | Schwaben (Mil.) | |
| 12/21/42 | Gallatin (W. Pa.) | 6 : 5 (aet) | Castle Shannon (W. Pa.) | |
| 12/21/42 | Morgan Strasser (W. Pa.) | 7 : 0 | Cuddy (W. Pa.) | |
| Croatian Eagles (Mil.) | bye | |||
| Hungarian American SC (Det.) | ||||
| ??? | ||||
| Round of 16 | ||||
| Eastern Bracket | ||||
| 1/24/43 | Kearny Celtic | 2 : 1 | Kearny Scots | |
| 1/24/43 | Philadelphia Americans | 5 : 1 | Philadelphia Nationals | |
| 2/7/43 | New York Americans | 2 : 3 | Brooklyn Wanderers | |
| 1/24/43 | Brooklyn Hispano | 4 : 3 | Brookhattan | |
| Eastern Bracket | ||||
| 3/14/43 | Sparta SC | 4 : 1 | Slovak SC | |
| 1/31/43 | Morgan Strasser | 4 : 1 | Gallatin | |
| 4/11/43 | Falk Field Club | 2 : 1 | Croatian Eagles | |
| Hungarian American SC | ||||
| Quarterfinals | ||||
| 2/21/43 | Philadelphia Americans | 1 : 0 | Brooklyn Wanderers | |
| 2/21/43 | Brooklyn Hispano | 3 : 1 | Kearny Celtic | |
| 4/25/43 | Sparta SC | 2 : 0 | Falk Field Club | |
| 3/6/43 | Hungarian American SC | 1 : 7 | Morgan Strasser | |
| Semifinals | ||||
| 3/14/43 | Brooklyn Hispano | 3 : 1 | Philadelphia Americans | |
| 5/9/43 | Sparta SC | 0 : 5(aet) | Morgan Strasser | |
| Final | ||||
| at Starlight Park – Bronx, New York | ||||
| 5/24/43 | Brooklyn Hispano | 2 : 2(aet) | Morgan Strasser | |
| REPLAY – at Starlight Park – Bronx, New York | ||||
| 5/30/43 | R | Brooklyn Hispano | 3 : 2 | Morgan Strasser |
| Brooklyn Hispano win National Challenge Cup on 5-4 aggregate | ||||
| KEY – w/o – Walkover, R – Replay, 1L – 1st Leg, 2L – 2nd Leg, 3L – 3rd Leg | ||||