| First Round | ||||
| Southern New York | ||||
| 11/2/19 | Robins Dry Dock | 3 : 2 | Morse Dry Dock | |
| 11/2/19 | Interborough Rapid Transit | 1 : 0 | Longfellows FC | |
| 11/2/19 | Greenpoint FC | 1 : 2 | New York FC | |
| Clan McDuff | 0 : 1 | Newburgh Shipyards | ||
| New Jersey | ||||
| 11/2/19 | American FC | 5 : 3 | Victor AA | |
| Bunker Hill | 1 : 3 | Paterson FC | ||
| Haledon Thistles | 1 : 2 | Babcock & Wilcox | ||
| 11//19 | Malta FC | 7 : 2 | Edison AFC | |
| Erie AA | w/o | West Hudson FC | ||
| Southern New England | ||||
| Crompton FC | 4 : 1 | J & P Coats | ||
| New Bedford Celtics | 0 : 0 | St. Michael’s FC | ||
| Fairlawn Rovers | 2 : 3 | Greystone Life Savers | ||
| Northern Massachusetts | ||||
| 11/2/19 | Abbot Worsted | 3 : 2 | Lynn Hibernains | |
| United Shoe | 6 : 1 | Andover United | ||
| General Electric | 0 : 2 | Fore River FC | ||
| 11/1/19 | Lynn Thistles | * | Lawrence League | |
| Boston City | 0 : 2 | Squantum | ||
| Connecticut | ||||
| Sons of St. George | vs. | Bridgeport Thistles | ||
| 11/2/19 | Bridgeport City | 2 : 1 | Bridgeport Rovers | |
| Eastern Pennsylvania | ||||
| 11//19 | J & J Dobson AA | 8 : 1 | Viscose FC | |
| 11//19 | New York Ship | 3 : 0 | Sun Ship AFC | |
| 11/2/19 | Merchants Ship | 5 : 1 | Germantown Boys | |
| 11/15/19 | Bethlehem Steel | 7 : 1 | Puritan YML | |
| 11//19 | Wolfenden Shore | 2 : 4 | Wanderers FC | |
| Western Pennsylvania | ||||
| Madison FC | 4 : 2 | Beadling | ||
| Cuddy FC | vs. | Pittsburgh Terminal | ||
| Ohio | ||||
| 11/2/19 | Magyar American FC | 6 : 1 | Goodrich FC | |
| 11/2/19 | Goodyear FC | 2 : 1 (aet) | White Motor | |
| 11//19 | Firestone FC | 0 : 1 | Bricklayers | |
| Illinois | ||||
| 11//19 | Harvey FC | 0 : 1 | Thistle FC | |
| 11/3/19 | Magyar FC | 0 : 6 | Palmer Park | |
| 11/3/19 | Bricklayers FC | 3 : 1 | Rangers AC | |
| Second Round | ||||
| Southern New York & New Jersey | ||||
| 11/27/19 | New York FC | 1 : 0 | Paterson FC | |
| 11/23/19 | Babcock & Wilcox | 2 : 1 | Interborough Rapid Transit | |
| Newburgh Shipyards | 4 : 2 | American FC | ||
| Malta AC | 0 : 2 | Tebo Yacht Basin | ||
| Erie AA | 8 : 1 | West Side AFC | ||
| 11/30/19 | Federal Ship | 2 : 3 | Robins Dry Dock | |
| Eastern Pennsylvania | ||||
| 11/29/19 | Bethlehem Steel | 3: 0 | Merchant Ship | |
| Wanderers | 3 : 1 | Disston AA | ||
| 11//19 | New York Ship | 2 : 2 | J & J Dobson AA | |
| Southern New England | ||||
| Fall River Rovers | 4 : 1 | Greystone Life Savers | ||
| New Bedford Celtics | 1 : 3 | J & P Coats | ||
| Northern Massachusetts | ||||
| 11//19 | Chicopee Rovers | 0 : 1 | Fore River FC | |
| Lynn Thistles | vs. | Squantum FC | ||
| United Shoe | 2 : 1 | Abbot Worsted | ||
| Connecticut | ||||
| New Haven FC | 3 : 1 | Bridgeport Swedish AC | ||
| Sons of St. George | 2 : 4 | Bridgeport City | ||
| Western Pennsylvania | ||||
| Pittsburgh Terminal Coal FC | 5 : 2 | Madison FC | ||
| McKeesport National Tube | w/o | Cuddy AA | ||
| Northwestern New York | ||||
| Oneida Community | 1 : 1 | McNaughton Rangers | ||
| Rochester City Moose | 1 : 0 | Rochester Celtics | ||
| Ohio | ||||
| Ideal Tire & Rubber | 1 : 2 | Goodyear FC | ||
| 11/30/19 | Bricklayers FC | 3 : 1 | Magyar American FC | |
| Michigan | ||||
| Packard FC | 3 : 1 | Bricklayers FC | ||
| Pontiac City FC | 7 : 0 | Vikings FC | ||
| Rising Star FC | 0 : 0 | Detroit SFC | ||
| Caledonia FC | 4 : 0 | Roses FC | ||
| Illinois | ||||
| Palmer Park | 5 : 1 | Thistles AFC | ||
| Lake Forest FC | 1 : 4 | Lincoln Park FC | ||
| 11/23/19 | Olympia FC | 5 : 1 | Thistle FC | |
| 11/23/19 | Bricklayers FC | 1 : 0 | Swedish American FC | |
| Missouri | ||||
| Ben Miller FC | 6 : 1 | Innisfalls FC | ||
| Scullin Steel | 3 : 1 | St. Louis Screw | ||
| Third Round | ||||
| Eastern Bracket | ||||
| 12/24/19 | Robins Dry Dock | 3 : 1 | Tebo Yacht Basin | |
| 12/29/19 | New York FC | 1 : 1* | Erie AA | |
| *match stopped after 70 minutes due to broken crossbar, replay ordered | ||||
| 1/6/20 | R | New York FC | 2 : 1 (aet) | Erie AA |
| 12/27/19 | Bethlehem Steel | 1 : 0 | New York Ship | |
| 12/28/19 | Fore River Rovers | 3 : 1 | J & P Coats | |
| 1/1/20 | Babcock & Wilcox | 0 : 1 | Newburgh Shipyards | |
| 1/1/20 | Lynn Thistles | 0 : 2 | Fall River Rovers | |
| 1/1/20 | United Shoe | 3 : 1 | New Haven | |
| 1/5/20 | Bridgeport City | 0 : 4 | Wanderers FC | |
| Western Bracket | ||||
| 12/25/19 | Rochester City Moose | 3 : 1 | McNaughton Rangers | |
| 1/4/20 | Ben Miller FC | 2 : 1 | Scullin Steel | |
| 1/5/20 | Packard FC | 2 : 1 | Rising Star FC | |
| 1/8/20 | Bricklayers FC (Cle.) | 1 : 3 | Goodyear FC | |
| 1/8/20 | Pittsburgh Terminal | 1 : 2 | McKeesport National Tube | |
| 3/20/20 | Olympia FC | 3 : 3 (aet) | Palmer Park | |
| 3/31/20 | R | Olympia FC | 3 : 1 | Palmer Park |
| 3/29/20 | Pontiac City | 0 : 8 | Caledonia FC | |
| Bricklayers FC (Chi.) | w/o | Lincoln Park FC | ||
| Fourth Round | ||||
| Eastern Bracket | ||||
| 3/20/20 | Bethlehem Steel | 10 : 0 | Wanderers FC | |
| 3/22/20 | Robins Dry Dock | 4 : 0 | Fall River Rovers | |
| 3/27/20 | Fore River Rovers | 3 : 0 | United Shoe | |
| 3/28/20 | New York FC | 2 : 1 | Newburg Shipyards | |
| Western Bracket | ||||
| 2/6/20 | Goodyear FC | 1 : 2 | Rochester City Moose | |
| 2/10/20 | Ben Miller FC | 3 : 2 | McKeesport FC | |
| 3/28/20 | Bricklayers & Masons | 1 : 2 | Olympia FC | |
| Packard FC | 3 : 2 | Caledonia FC | ||
| Quarterfinals | ||||
| 4/4/20 | Robins Dry Dock | 1 : 0 | Bethlehem Steel | |
| 4/5/20 | Ben Miller FC | 2 : 1 | Olympia FC | |
| 4/5/20 | Fore River Rovers | 3 : 0 | New York FC | |
| 4/23/20 | Packard FC | 5 : 1 | Rochester City Moose | |
| Semifinals | ||||
| 4/10/20 | Fore River Rovers | 2 : 0 | Robins Dry Dock | |
| 4/25/20 | Ben Miller FC | 4 : 2 | Packard FC | |
| Final | ||||
| at Handlan’s Park, St. Louis, Missouri | ||||
| 5/8/20 | Ben Miller FC | 2 : 1 | Fore River Rovers | |
| KEY – w/o – Walkover, R – Replay | ||||
