| 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 | ||||
Baltimore Americans
1945 National Challenge Cup Results
| Round of 32 | ||||
| Eastern Bracket | ||||
| 5/14/45 | Brookhattan | 3 : 1 (aet) | New York Americans | |
| 3/18/45 | Brooklyn Hispano | 2 : 0 | German American AC | |
| 3/11/45 | Brooklyn Wanderers | 4 : 3 | Eintracht SC (NYC) | |
| 5/14/45 | Kearny Irish | 2 : 1 | Kearny Scots | |
| 4/1/45 | Baltimore Americans | 4 : 0 | Ruggiero SC (Bal.) | |
| 3/4/45 | Baltimore SC | 11 : 0 | Phoenix SC (Phi.) | |
| Philadelphia Americans | ||||
| Philadelphia Nationals | ||||
| Western Bracket | ||||
| 4/1/45 | Slovak SC (Chi.) | 1 : 0 | Sparta (Chi.) | |
| 4/1/45 | Viking AA (Chi.) | 2 : 1 | Hakoah Center (Chi.) | |
| 3/11/45 | Cleveland Americans | 11 : 2 | Rochester Celtics | |
| 5/2/45 | Gallatin (W. Pa.) | 3 : 0 | Morgan Strasser (W. Pa.) | |
| United German Americans (Det.) | ||||
| ??? | ||||
| 4/1/45 |
Raftery Painters (St. L) | 5 : 3 |
National Slug (St. L) | |
| Croatian Eagles (Mil.) | bye | Only Wisconsin Entry | ||
| Round of 16 | ||||
| Eastern Bracket | ||||
| 5/20/45 | Brookhattan | 2 : 1 | Kearny Irish | |
| 5/13/45 | Brooklyn Hispano | 4 : 3 (aet) | Brooklyn Wanderers | |
| 5/13/45 | Philadelphia Americans | 3 : 2 | Philadelphia Nationals | |
| 4/8/45 | Baltimore Americans | 1 : 0 | Baltimore SC | |
| Western Bracket | ||||
| 4/29/45 | Viking AA | 4 : 2 (aet) | Slovak SC | |
| 5/6/45 | Raftery Painters | 4 : 1 | Croatian Eagles | |
| United German Americans | ||||
| 5/13/45 | Cleveland Americans | 2 : 1 (aet) | Gallatin | |
| Quarterfinals | ||||
| 5/25/45 | Brooklyn Hispano | 4 : 3 | Philadelphia Americans | |
| 5/25/45 | Brookhattan | 3 : 2 | Baltimore Americans | |
| 5/27/45 | Viking A.A. | 3 : 6 |
Raftery Painters | |
| 5/27/45 | United German Americans | 1 : 2 | Cleveland Americans | |
| Semifinals | ||||
| 6/4/45 | Brookhattan | 5 : 4(aet) | Brooklyn Hispano | |
| 6/3/45 | Raftery Painters | 0 : 2 | Cleveland Americans | |
| Final | ||||
| First Leg – Starlight Park – Bronx, New York | ||||
| 6/10/45 | Brookhattan | 4 : 1 | Cleveland Americans | |
| Second Leg -at Shaw Field – Cleveland, Ohio | ||||
| 6/16/45 | Cleveland Americans | 1 : 2 | Brookhattan | |
| Brookhattan win National Challenge Cup on 6-2 aggregate | ||||
| KEY – w/o – Walkover, R – Replay, 1L – 1st Leg, 2L – 2nd Leg, 3L – 3rd Leg | ||||
1944 National Challenge Cup Results
| Round of 32 | ||||
| Eastern Bracket | ||||
| 1/2/44 | Brooklyn Hispanio | 4 : 0 | Brooklyn Germans | |
| 1/9/44 | Brooklyn Wanderers | 2 : 1 | New York Sport Club | |
| 1/2/44 | Brookhattan | 2 : 4 | Eintracht SC (NYC) | |
| 1/9/44 | New York Americans | 4 : 1 (aet) | German American SC (NYC) | |
| 1/2/44 | Kearny Scots | 4 : 3 | Hoboken SC (NJ) | |
| 1/16/44 | Kearny Celtic | 5 : 1 | Elizabeth SC | |
| 1/23/44 | Baltimore Americans | 6 : 3 | Baltimore SC | |
| 1/23/44 | Philadelphia Americans | 6 : 4 | Philadelphia Nationals | |
| Western Bracket | ||||
| 1/2/44 | Avella (W. Pa.) | 1 : 0 | Gallatin (W. Pa.) | |
| 1/23/44 | Cleveland Americans | 6 : 2 | German American SC (Buff.) | |
| Detroit All Stars | ||||
| 12/19/43 | Viking AA (Chi.) | 4 : 0 | Swedish American SC (Chi.) | |
| 12/12/43 | Sparta (Chi.) | 2 : 0 | Schwaben (Chi.) | |
| Falk SC (Mil.) | Bye | |||
| Croatian Eagles (Mil.) | Bye | |||
| Morgan Strasser (W. Pa.) | Bye | |||
| Round of 16 | ||||
| Eastern Bracket | ||||
| 1/23/44 | Kearny Scots | 1 : 1 (aet) | Kearny Celtic | |
| 1/30/44 | R | Kearny Scots | 1 : 2 | Kearny Celtic |
| 1/30/44 | New York Americans | 1 : 4 | Eintracht SC | |
| 1/23/44 | Brooklyn Wanderers | 3 : 3 | Brooklyn Hispano | |
| 1/30/44 | R | Brooklyn Wanderers | 4 : 4 (aet) | Brooklyn Hispano |
| 2/6/44 | R | Brooklyn Wanderers | 3 : 2 (aet) | Brooklyn Hispano |
| 1/30/44 | Philadelphia Americans | 1 : 2 (aet) | Baltimore Americans | |
| Western Bracket | ||||
| 2/6/44 | Morgan Strasser | 2 : 0 | Avella | |
| 2/27/44 | Detroit All Stars | 5 : 1 | Cleveland Americans | |
| 1/16/44 | Viking AA | 3 : 2 | Sparta | |
| 1/2/44 | Falk SC | 4 : 0 | Croatian Eagles | |
| Quarterfinals | ||||
| 2/20/44 | Eintracht S.C. | 0 : 3 | Brooklyn Hispano | |
| 2/20/44 | Kearny Celtic | 2 : 0 | Baltimore Americans | |
| 3/12/44 | Detroit All Stars | 1 : 2 | Morgan Strasser | |
| 3/26/44 | Falk Field Club | 1 : 1 (aet) | Viking A.A. | |
| 4/9/44 | R | Viking A.A. | 3 : 1 | Falk Field Club |
| Semifinals | ||||
| 3/5/44 | Brooklyn Hispano | 3 : 0 | Kearny Celtic | |
| 4/23/44 | 1L | Viking A.A. | 0 : 2 | Morgan Strasser |
| 5/9/44 | 2L | Morgan Strasser | 9 : 0 | Viking A.A. |
| Morgan Strasser advance on 11-0 aggregate | ||||
| Final | ||||
| at The Polo Grounds – New York, New York | ||||
| 5/14/44 | Brooklyn Hispano | 4 : 0 | Morgan Strasser | |
| KEY – w/o – Walkover, R – Replay, 1L – 1st Leg, 2L – 2nd Leg, 3L – 3rd Leg | ||||