| 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 | |||||