| 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 | ||||
Newark Skeeters
1923-1924 National Challenge Cup Results
| Third Round | ||||
| Eastern Bracket | ||||
| 12/1/23 | Bethlehem Steel | 5 : 0 | Philadelphia Field Club | |
| 12/1/23 | Holyoke Falco | 1 : 1 (aet) | Roxbury FC | |
| 12/8/23 | R | Roxbury FC | 0 : 3 | Holyoke Falco |
| 12/2/23 | New York National Giants | 1 : 0 | Ansonia FC (CT) | |
| 12/2/23 | Newark Skeeters | 3 : 2 | British War Veterans (Trenton) | |
| 12/2/23 | Fall River Marksmen | 8 : 1 | Prospect Hill FC (MA) | |
| 12/3/23 | New York Field Club | 1 : 0 | Brooklyn Wanderers | |
| Waypoyset FC (RI) | 2 : 1 |
Fairlawn Rovers | ||
| Abbot Worsted | W : L | Pacific Mills | ||
| Western Bracket | ||||
| 12/2/23 | Thistles FC (Chi.) | 1 : 0 | Olympia FC (Chi.) | |
| 12/16/23 | Goodyear FC (Akron) | 2 : 1 | Favorite Knits (Cle.) | |
| 12/23/23 | MacKenzie FC (Akron) | 3 : 0 | Rochester City Moose | |
| Vesper Buick (St. L) | 3 : 2 | Ben Miller A.C. (St. L) | ||
| Harmarville FC (Pit.) | 3 : 1 | Jeanette FC (Pit.) | ||
| Pilgrims FC (Det.) | L : W | Toledo SC | ||
| Celtic FC (Det.) | W : L | Caledonia FC (Det.) | ||
| Bricklayers & Masons (Chi.) | 1 : 0 | Chicago Field Club | ||
| Fourth Round | ||||
| Eastern Bracket | ||||
| 12/15/23 | Bethlehem Steel | 2 : 2 (aet) | New York Field Club | |
| 12/30/23 | R | Bethlehem Steel | 4 : 3 | New York Field Club |
| 12/22/23 | Abbot Worsted | 1 : 0 (aet) | Holyoke Falco | |
| 12/23/23 | Fall River Marksmen | 3 : 0 | Wayposet FC | |
| 12/25/23 | Newark Skeeters | 5 : 2 | New York National Giants | |
| Western Bracket | ||||
| 12/23/23 | Goodyear FC | 1 : 0 | MacKenzie FC | |
| 12/30/23 | Vesper Buick | 3 : 0 | Harmarville FC | |
| 1/14/24 | Thistle FC | 1 : 2 | Bricklayers FC | |
| Toledo FC | L : W | Celtic FC | ||
| Quarterfinals | ||||
| 1/19/24 | Fall River Marksmen | 2 : 1 | Abbot Worsted | |
| 1/26/24 | Bethlehem Steel | 1 : 1 (aet) | Newark Skeeters | |
| 2/1/24 | R | Bethlehem Steel | 6 : 0 | Newark Skeeters |
| 2/10/24 | Vesper Buick | 7 : 1 | Goodyear FC | |
| 3/2/24 | Bricklayers & Masons | 1 : 0 | Celtic FC | |
| Semifinals | ||||
| 3/9/24 | Fall River Marksmen | 2 : 0 | Bethlehem Steel | |
| 3/16/24 | Vesper Buick | 5 : 0 | Bricklayers & Masons | |
| Final | ||||
| at High School Field – St. Louis, Missouri | ||||
| 3/30/24 | Fall River Marksmen | 4 : 2 | Vesper Buick | |
| KEY – w/o – Walkover, R – Replay | ||||