| 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 | ||||