| First Round | ||||
| Eastern Bracket | ||||
| Northern Massachusetts | ||||
| 10/16/20 | Lynn Gas & Electric | 7 : 1 | Trimo FC | |
| 10/16/20 | Fore River FC | 1 : 2 | General Electric FC | |
| *replay orderd due to rules violations by General Electric FC | ||||
| 10/30/20 | R | Fore River FC | 5 : 0 | General Electric FC |
| 10/16/20 | Arlington Mills | 1 : 2 | Boston City | |
| 10/16/20 | Abbot Worsted | 9 : 0 | Chicopee Rovers | |
| 10/16/20 | Hendee Indians | 4 : 1 | Smith & Dove FC | |
| 10/16/20 | Farr Alpaca | 4 : 2 | United Shoe | |
| Southern New England | ||||
| 10/16/20 | St. Michael’s | 1 : 1 | Saylesville FC | |
| 10/30/20 | R | St. Michael’s | 1 : 1 | Saylesville FC |
| 11/7/20 | R | St. Michael’s | 3 : 1 | Saylesville FC |
| 10/16/20 | J & P Coats | 1 : 1 | Fall River Rovers | |
| 10/30/20 | R | J & P Coats | 1 : 2 | Fall River Rovers |
| 10/16/20 | Ashton & Berkeley | 3 : 2 | Clan Cameron | |
| Connecticut | ||||
| 10/17/20 | Hartford S.K.F. | 1 : 0 | New Departure FC | |
| Southern New York | ||||
| 10/17/20 | New York FC | 0 : 1 | Tebo Yacht Basin | |
| New Jersey | ||||
| 10/17/20 | Erie Juniors FC | 0 : 5 | Erie AA | |
| 10/17/20 | Federal Shipyards | 8 : 2 | Athenia Steel | |
| 10/17/20 | Babcock & Wilcox | 2 : 4 | Sprague FC | |
| 10/17/20 | Bunker Hill | 1 : 4 | Paterson FC | |
| Eastern Pennsylvania | ||||
| 10/16/20 | J & J Dobson | 4 : 3 | Wolfenden Shore | |
| 10/16/20 | North End FC | 0 : 6 | Disston AA | |
| 10/16/20 | Hibernains FC | 1 : 6 | Bethlehem Steel | |
| Western Bracket | ||||
| Michigan | ||||
| 10/17/20 | Solvay FC | 1 : 5 | Pontiac City | |
| Ohio | ||||
| 10/16/20 | Firestone FC | 0 : 1 | Goodrich FC | |
| Western Pennsylvania | ||||
| 10/17/20 | Dunlevy S.C. | 2 : 0 | H.R. Gieb Trainworks | |
| Second Round | ||||
| Eastern Bracket | ||||
| Northern Massachusetts | ||||
| 11/6/20 | Maple Leaf FC | 0 : 3 | Gray & Davis | |
| 11/6/20 | Farr Alpaca | 0 : 2 | Boston City | |
| 11/6/20 | Lynn Gas & Electric | 3 : 2 | Hendee Indians | |
| 11/20/20 | Abbot Worsted | 0 : 1 | Fore River Rovers | |
| Southern New England | ||||
| 10/30/20 | Potter & Johnson | 3 : 2 | Colonial FC | |
| 11/6/20 | Fairlawn Rovers | 3 : 0 | Ashton & Berkley | |
| 11/13/20 | Greystone FC | 1 : 8 | Fall River Rovers | |
| 11/13/20 | Young Thornton | 2 : 4 | St. Michael’s | |
| Connecticut | ||||
| 11/7/20 | Columbia Gramaphone | 4 : 1 | Hartford S.K.F. | |
| 11/7/20 | Ansonia FC | 3 : 1 | Stamford FC | |
| Southern New York | ||||
| 11/2/20 | Tebo Yacht Basin | 2 : 1 | Brooklyn FC | |
| 11/7/20 | Robins Dry Dock | 4 : 0 | Clan MacDuff | |
| New Jersey & Eastern Pennsylvania | ||||
| 11/6/20 | Erie AA | 4 : 3 | Bethlehem Steel | |
| 11/6/20 | Disston AA | 1 : 1 | J & J Dobson FC | |
| 11/13/20 | R | J & J Dobson FC | 1 : 1 | Disston AA |
| 11/20/20 | R | Disston AA | 1 : 3 | J & J Dobson FC |
| 11/7/20 | Paterson FC | 4 : 1 | Sprague FC | |
| 11/7/20 | Cedar Cliff FC | 1 : 7 | Federal Ship FC | |
| Western Bracket | ||||
| Northwestern New York | ||||
| 11/7/20 | Rochester City Moose | 1 : 0 | Rochester Celtic | |
| 11/7/20 | McNaughton Rangers | 3 : 1 | Camera Works FC | |
| 11/14/20 | Oneida Community FC | 0 : 1 | Kodak Park FC | |
| Western Pennsylvania | ||||
| 11/7/20 | Madison FC | 2 : 1 | Dunlevy FC | |
| Ohio | ||||
| 11/7/20 | Goodrich FC | 2 : 1 | White Motors FC | |
| 11/7/20 | Greyhounds FC | 1 : 1 | Goodyear FC | |
| 11/14/20 | R | Goodyear FC | 1 : 1 | Greyhounds FC |
| 11/21/20 | R | Greyhounds FC | 1 : 3 | Goodyear FC |
| Michigan | ||||
| 11/7/20 | I.F.L. FC | 0 : 0 | Roses FC | |
| 11/14/20 | R | Roses FC | 2 : 1 | I.F.L. FC |
| 11/7/20 | Magyar FC | 0 : 2 | Ulster FC | |
| 11/7/20 | Pontiac City | 5 : 0 | One and All FC | |
| 11/7/20 | Walkerville FC | 2 : 4 | Caledonian FC | |
| Illinois & Wisconsin | ||||
| 11/7/20 | Simco FC | 2 : 0 | Pullman FC | |
| 11/7/20 | Rangers FC | 0 : 2 | Thistles FC | |
| 11/7/20 | Swedish American AA | 0 : 0 | Harvey FC | |
| 11/14/20 | R | Swedish American AA | 3 : 1* | Harvey FC |
| *Harvey FC protested, replay ordered | ||||
| 11/21/20 | R | Harvey FC | 1 : 0 | Swedish American AA |
| 11/7/20 | Norwegian American AA | 1 : 8 | Bricklayers FC | |
| Missouri | ||||
| 11/25/20 | Ben Miller FC | 2 : 5 | Innisfall FC | |
| 11/25/20 | St. Louis Screw | 3 : 3* | Scullin Screw | |
| *St. Louis Screw disqualified for ineligible players, Scullin Screw awarded match | ||||
| Third Round | ||||
| Eastern Bracket | ||||
| 11/25/20 | Tebo Yacht Basin | 8 : 2 | Ansonia S.C. | |
| 11/27/20 | Potter & Johnson | 0 : 1(aet) | Fairlawn Rovers | |
| 11/27/20 | Grey & Davis | 0 : 3 | Fore River FC | |
| 11/27/20 | Lynn Gas & Electric | 3 : 1 | Boston City | |
| 11/27/20 | J & J Dobson | 2 : 1 | Paterson FC | |
| 11/28/20 | Erie AA | 3 : 1 | Federal Shipyards | |
| 11/28/20 | Robins Dry Dock | 3 : 0 | Columbia Graphophone | |
| 12/4/20 | St. Micheal’s Club | 0 : 4 | Fall River Rovers | |
| Western Bracket | ||||
| 11/28/20 | Pontiac City | 2 : 3 | Caledonian FC | |
| 11/28/20 | Goodrich FC | 2 : 1 | Goodyear FC | |
| 11/28/20 | McNaughton Rangers | 0 : 4 | Kodak Park FC | |
| 11/28/20 | Madison S.C. | 3 : 1 | Rochester City Moose | |
| 11/28/20 | Harvey FC | 2 : 1 | Thistles FC | |
| 11/28/20 | Simco FC | 0 : 2 | Bricklayers FC | |
| 11/28/20 | Roses FC | 3 : 0 | Ulster FC | |
| 12/12/20 | Innisfall FC | 1 : 3 | Scullin Steel | |
| Fourth Round | ||||
| Eastern Bracket | ||||
| 12/18/20 | Fore River FC | 3 : 1 | Fall River Rovers | |
| 12/18/20 | Fairlawn Rovers | 3 : 1 | Lynn Gas & Electric | |
| 12/18/20 | Tebo Yach Basin | 1 : 0 | J & J Dobson | |
| 12/19/20 | Robins Dry Dock | 1 : 1 | Erie AA | |
| 12/26/20 | R | Robins Dry Dock | 5 : 3 | Erie AA |
| Western Bracket | ||||
| 12/12/20 | Caledonian FC | 2 : 1 | Roses FC | |
| 12/12/20 | Harvey FC | 1 : 1 | Bricklayers FC | |
| 12/19/20 | R | Bricklayers FC | 5 : 0 | Harvey FC |
| 12/25/20 | Scullin Steel | 3 : 0 | Madison SC | |
| 12/26/20 | Goodrich FC | w/o | Kodak Park FC | |
| Quarterfinals | ||||
| 12/23/20 | Caledonian FC | 2 : 1 | Goodrich FC | |
| 1/15/21 | Tebo Yacht Basin | 3 : 1 | Fairlawn Rovers | |
| 1/23/21 | Bricklayers FC | 1 : 1 | Scullin Steel | |
| 3/5/21 | Robins Dry Dock | 3 : 0 | Fore River FC | |
| 1/30/21 | R | Scullin Steel | 2 : 1 | Bricklayers FC |
| *replay ordered after Bricklayers protest was upheld | ||||
| 3/6/21 | R | Scullin Steel | 2 : 0 | Bricklayers FC |
| Semifinals | ||||
| 3/12/21 | Scullin Steel | 2 : 1 | Caledonia FC | |
| 3/27/21 | Robins Dry Dock | 3 : 0 | Tebo Yacht Basin | |
| Final | ||||
| at Fall River Athletic Field – Fall River, Massachusetts | ||||
| 4/19/21 | Robins Dry Dock | 4 : 2 | Scullin Steel | |
| KEY – w/o – Walkover, R – Replay | ||||