| 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 | |||||
Holley Carburetor
1929 National Challenge Cup Results
| First Round | |||||
| Eastern Bracket | |||||
| 2/3/29 | Waterbury (CT) | 1 : 6 | Walsh Chevrolet (Fall River) | ||
| 2/3/29 | Trenton FC | 8 : 1 | Newark Skeeters | ||
| 2/3/29 | Canton FC (Bal.) | 0 : 5 | Bethlehem Steel | ||
| 2/3/29 | New York Hakoah | 7 : 1 | Mamaronek FC | ||
| 2/3/29 | New York Giants | 4 : 1 | IRT Rangers | ||
| 2/3/29 | Rochester Celtic | 3 : 2 | Hungarian SC (Buffalo) | ||
| 2/3/29 | Hungaria Sport Club (NYC) | w/o | First German SC (NYC) | ||
| 2/3/29 | Newark Portuguese | 3 : 0 | Bayonne Rovers | ||
| Western Bracket | |||||
| 12/16/28 | Sparta A & BA (Chi.) | 3 : 0 | Carpenters FC (Chi.) | ||
| 12/16/28 | Madison Kennels (St. L) | 4 : 1 | Ben Miller SC (St. L) | ||
| 12/23/28 | Tablers FC (St.L) | 5 : 2 | Wellston FC (St. L) | ||
| 12/30/28 | Bricklayers FC (Chi.) | 2 : 0 | Buda AA (Ill.) | ||
| 12/23/28 | Wood Hydraulic (Det.) | 1 : 3 | All Scots FC (Det.) | ||
| 12/23/28 | Holley Carburetor (Det.) | 2 : 0 | Flint IMA (Mich.) | ||
| Goodyear FC (Akron) | 4 : 1 | Celtics FC (Cle.) | |||
| 12/23/28 | Thistles FC (Chi.) | 1 : 1 (aet) | Olympia (Chi.) | ||
| R | Thistles FC | W : L | Olympia | ||
| Second Round | |||||
| Eastern Bracket | |||||
| 2/16/29 | Bethlehem Steel | 5 : 0 | Walsh Chevrolet | ||
| 2/17/29 | New York Hakoah | 6 : 0 | Rochester Celtic | ||
| 2/17/29 | Newark Portuguese | 4 : 1 | New York Hungaria | ||
| 2/17/29 | Bricklayers FC | 3 : 1 | Tablers FC | ||
| Western Bracket | |||||
| 2/17/29 | Madison Kennels | 5 : 1 | Thistles FC | ||
| 2/23/29 | Holley Carburetor | 10 : 3 | Goodyear FC | ||
| 2/24/29 | New York Giants | 8 : 0 | Trenton FC | ||
| 2/24/29 | Sparta A & BA | 7 : 0 | All Scots FC | ||
| Quarterfinals | |||||
| 3/3/29 | New York Giants | 2 : 2 | Bethlehem Steel | ||
| 3/9/29 | R | Bethlehem Steel | 2 : 6 | New York Giants | |
| 3/3/29 | Sparta A & BA | 3 : 1 (aet) | Bricklayers FC | ||
| 3/17/29 | New York Hakoah | 3 : 2 | Newark Portuguese | ||
| 3/10/29 | Madison Kennels | 5 : 1 | Holley Carburetor | ||
| Semifinals | |||||
| 3/17/29 | Madison Kennels | 7 : 4 | Sparta A & BA | ||
| 3/24/29 | New York Hakoah | 1 : 0 | New York Giants | ||
| Final | |||||
| First Leg – at Sportsman’s Park – St.Louis, Missouri | |||||
| 3/31/29 | Madison Kennels | 0 : 2 | New York Hakoah | ||
| Second Leg – at Dexter Park – Brooklyn, New York | |||||
| 4/7/29 | New York Hakoah | 3 : 0 | Madison Kennels | ||
| Hakoah All Stars win National Challenge Cup on 5-0 aggregate | |||||
| KEY – w/o – Walkover, R – Replay | |||||
1927 National Challenge Cup Results
| First Round | ||||
| *advanced from qualifying rounds. All other clubs exempt from qualifying | ||||
| Eastern Bracket | ||||
| 3/17/27 | Brooklyn Wanderers | 1 : 2 | Newark Skeeters | |
| 3/26/27 | Bethlehem Steel | 3 : 1 | Philadelphia Field Club | |
| 3/26/27 | Fore River FC* | 3 : 2 (aet) | Boston Wonder Workers | |
| 3/27/27 | Fall River Marksmen | 3 : 2 | New Bedford Whalers | |
| 3/27/27 | Indiana Flooring | 3 : 1 | New York Giants | |
| 3/27/27 | Providence Clamdiggers | 3 : 3 (aet) | J & P Coats | |
| 4/2/27 | R | J & P Coats | 2 : 3 | Providence Clamdiggers |
| 3/27/27 | Trenton Field Club* | 2 : 1 | Viking A.C. (NYC)* | |
| 3/27/27 | Hungarian FC (Buff.)* | 0 : 5 | Whittall Carpet Mill* | |
| Though eliminated in qualifying rounds, Whittall Carpet Mill were allowed to re-enter, | ||||
| due to the withdrawal of Springfield Babes from the ASL | ||||
| Western Bracket | ||||
| 2/20/27 | Ben Miller FC (St. L) | 5 : 4 | Pants Store FC (St. L) | |
| 2/20/27 | Sparta A & BA (Chi.) | 3 : 0 | Thistle FC (Chi.) | |
| 2/20/27 | Pullman FC (Chi.) | 0 : 4 | Buda A.A. (Harvey , Ill.)* | |
| 2/27/27 | Wellston FC (St. L) | 9 : 1 | Johnston City AFC (Ill.)* | |
| 2/27/27 | Bricklayers FC (Chi.) | 2 : 0 | White Banner Malt (St. L) | |
| 2/27/27 | Holley Carburetor (Det.)* | 2 : 1 | Canadian Club (Chi.) | |
| 2/27/27 | American Hungarian FC (Cle.) | 3 : 2 | Magyar American FC (Cle.)* | |
| 2/27/27 | MacKenzie FC (Akron) | 4 : 0 | Lorain Eagles (Oh.) | |
| Second Round | ||||
| Eastern Bracket | ||||
| 4/3/27 | Fall River Marksmen | 5 : 0 | Fore River FC | |
| 4/3/27 | Trenton FC | 0 : 6 | Bethlehem Steel | |
| 4/9/27 | Indiana Flooring | 1 : 2 (aet) | Newark Skeeters | |
| 4/9/27 | Providence Clamdiggers | 7 : 1 | Whittall Carpet Mill | |
| Western Bracket | ||||
| 3/20/27 | American Hungarian FC | 5 : 0 | MacKenzie FC | |
| 3/20/27 | Holley Carburetor | 3 : 2 | Buda A.A. | |
| 3/20/27 | Sparta A & BA | 2 : 1 | Bricklayers FC | |
| 3/13/27 | Ben Miller FC | 4 : 2 | Wellston FC | |
| Quarterfinals | ||||
| 4/3/27 | Holley Carburetor | 4 : 2 | American Hungarian FC | |
| 4/3/27 | Ben Miller FC | 2 : 2(aet) | Sparta A & BA | |
| 4/10/27 | R | Sparta A & BA | 1 : 0 | Ben Miller FC |
| 4/10/27 | Bethlehem Steel | 1 : 0 | Newark Skeeters | |
| 4/17/27 | Fall River Marksmen | 3 : 2 (aet) | Providence Clamdiggers | |
| Semifinals | ||||
| 4/18/27 | Sparta A & BA | 1 : 2 | Holley Carburetor | |
| 4/24/27 | Fall River Marksmen | 2 : 1 | Bethlehem Steel | |
| Final | ||||
| at University of Detroit Stadium – Detroit, Michigan | ||||
| 5/1/27 | Fall River Marksmen | 7 : 0 | Holley Carburetor | |
| KEY – w/o – Walkover, R – Replay | ||||