| First Round | ||||
| *advanced from qualifying rounds. All other clubs exempt from qualifying | ||||
| Eastern Bracket | ||||
| 1/16/26 | Boston Wonder Workers | 2 : 1 | Fore River FC* | |
| 1/16/26 | J & P Coats | 4 : 1 | Abbot Worsted | |
| 1/16/26 | New Bedford Whalers | 5 : 0 | Shawsheen Indians | |
| 1/17/26 | Newark Skeeters | 1 : 5 | Bethlehem Steel | |
| 1/17/26 | Brooklyn Wanderers | 2 : 2 (aet) | Indiana Flooring | |
| 1/24/26 | R | Indiana Flooring | 2 : 3 | Brooklyn Wanderers |
| 1/17/26 | Fall River Marksmen | 3 : 2 | Providence Clamdiggers | |
| 1/17/26 | New York Giants | 9 : 1 | Yonkers Thistle* | |
| 1/17/26 | Trenton FC* | 3 : 3 (aet) | Philadelphia Field Club* | |
| 1/24/26 | R | Trenton FC* | 1 : 4 | Philadelphia Field Club* |
| Western Bracket | ||||
| 1/10/26 | Wellston FC (St. L) | 1 : 2 | Pants Store FC (St. L) | |
| 1/17/26 | Gar Wood FC (Det.) | 3 : 4 | Canadian Club (Chi.) | |
| 1/17/26 | Olympia FC (Chi.) | 1 : 0 | Thistles FC (Chi.) | |
| 1/17/26 | Kenosha FC (Wis.) | 2 : 2 | Pullman FC (Chi.) | |
| 1/24/26 | R | Pullman FC | 4 : 0 | Kenosha FC |
| 1/17/26 | Bricklayers FC (Chi.) | 2 : 1 | Sparta A & BA (Chi.) | |
| 1/17/26 | Thistle FC (Cle.) | 1 : 2 | Clan MacKenzie (Akron) | |
| 1/17/26 | Vesper Buick (St. L) | 7 : 2 | Royalton Stars (St. L) | |
| 1/24/26 | Ben Miller SC (St. L) | 3 : 1 | Magyar American FC (Cle.) | |
| Second Round | ||||
| Eastern Bracket | ||||
| 2/13/26 | Philadelphia Field Club | 1 : 2 | Bethlehem Steel | |
| 2/14/26 | Fall River Marksmen | 1 : 1 | Boston Wonder Workers | |
| 2/21/26 | R | Fall River Marksmen | 2 : 3 | Boston Wonder Workers |
| 2/20/26 | New Bedford Whalers | 0 : 1 | J & P Coats | |
| 2/21/26 | Brooklyn Wanderers | 2 : 2 (aet) | New York Giants | |
| 2/28/26 | R | Brooklyn Wanderers | 1: 5 | New York Giants |
| Western Bracket | ||||
| 2/7/26 | Vesper Buick | 6 : 2 | Pants Store FC | |
| 2/7/26 | Ben Miller SC | w/o | Clan MacKenzie (Akron) | |
| *MacKenzie won 2-0. Ben Miller protested, and MacKenzie was DQ’d for using two ineligible players | ||||
| 2/7/26 | Pullman FC | 3 : 1 | Bricklayers FC | |
| 2/14/27 | Canadian Club | 1 : 1 (aet) | Olympia FC | |
| 2/21/26 | R | Canadian Club | 6 : 3 | Olympia FC |
| Quarterfinals | ||||
| 2/28/26 | Boston Wonder Workers | 3 : 5 | J & P Coats | |
| 3/7/26 | Ben Miller SC | 2 : 0 | Vesper Buick | |
| 3/14/26 | New York Giants | 1 : 2 | Bethlehem Steel | |
| 3/14/26 | Canadian Club | 1 : 1 (aet) | Pullman FC | |
| 3/21/26 | R | Canadian Club | 3 : 0 | Pullman FC |
| Semifinals | ||||
| 3/21/26 | J & P Coats | 1 : 3 | Bethlehem Steel | |
| 3/28/26 | Ben Miller SC | 2 : 0 | Canadian Club | |
| Final | ||||
| at Ebbets Field – Brooklyn, New York | ||||
| 4/11/26 | Bethlehem Steel | 7 : 2 | Ben Miller SC | |
| KEY – w/o – Walkover, R – Replay | ||||
Vesper Buick
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 | ||||