| First Round | ||||
| New York | ||||
| 10/20/18 | Morse Dry Dock | 4 : 0 | Standard Shipyard FC | |
| 10/20/18 | Robbins Dry Dock | 3 : 0 | Longfellows FC | |
| 10/20/18 | New York FC | w/o | Clan MacDuff FC | |
| 10/20/18 | Viking FC | w/o | Tebo FC | |
| New Jersey | ||||
| 10/27/18 | Scottish American FC (NJ) | 3 : 1 | Crescent Ship FC | |
| 10/27/18 | Federal Ship | 1 : 1 | Babcock & Wilcox | |
| 11/3/18 | R | Federal Ship | 3 : 1 | Babcock & Wilcox |
| 10/27/18 | Hog Island FC | 0 : 1 | Merchants Shipbuilding A | |
| 10/28/18 | Paterson FC | 8 : 1 | Kinley FC | |
| 11/3/18 | Jersey AC | 1 : 0 | Passaic Swedish AC | |
| Southern New England | ||||
| 11/2/18 | Pan American FC | 1 : 3 | J & P Coats | |
| Northern Massachusetts | ||||
| 10/26/18 | Boston Rovers | 3 :6 | Merrimac Valley FC | |
| 11/2/18 | Fisk Red Tops | 2 : 8 | Fore River FC | |
| Connecticut | ||||
| 10/20/18 | Bridgeport Swedish AC | 2 : 3 | Bridgeport City AFC | |
| Eastern Pennsylvania | ||||
| 11/2/18 | Disston AA | 5 : 7 | Merchants Shipbuilding B | |
| 11/13/18 | Bethlehem Steel | 3 : 0 | New York Shipbuilding | |
| Illinois | ||||
| 11/10/18 | Bricklayers & Masons FC | 3 : 1 | American Hungarian FC | |
| Second Round | ||||
| New Jersey & Eastern Pennsylvania | ||||
| 11/23/18 | Bethlehem Steel | 4 : 3 (aet) | Merchants Shipbuilding A | |
| 12/1/18 | Federal Shipbuilding | 2 : 1* | Merchants Shipbuilding B | |
| *Match ordered replayed after Merchants protest | ||||
| 12/25/18 | R | Federal Shipbuilding | 3 : 2 | Merchants Shipbuilding B |
| 12/1/18 | Scottish American FC (NJ) | 6 : 0 | Tietjen & Lang Dry Dock | |
| 12/1/18 | Paterson FC | 9 : 2 | Jersey AC | |
| Connecticut & New York | ||||
| 12/1/18 | Robins Dry Dock | 2 : 1 | Bridgeport City AFC | |
| 12/1/18 | Morse Dry Dock | w/o | Chinese Students FC | |
| 12/1/18 | New York FC | w/o | Viking FC | |
| Northern Massachusetts | ||||
| 11/23/18 | Fore River FC | 6 : 3 | Merrimac Valley | |
| Southern New England | ||||
| 11/16/18 | J & P Coats | 6 : 0 | Olneyville Oaks FC | |
| Western Pennsylvania | ||||
| 11/23/18 | Homestead Steel | w/o | Pittsburgh FC | |
| Pittsburgh FC withdraw due to World War I enlistments | ||||
| Michigan | ||||
| 11/10/18 | Roses FC | 4 : 0 | Solway FC | |
| 11/10/18 | Detroit FC | w/o | Corinthian FC | |
| Ohio | ||||
| 11/17/18 | Magyar American FC | 1 : 1 | Hydraulic Pressed Steel Company | |
| 11/24/18 | R | Magyar American FC | 3 : 2 | Hydraulic Pressed Steel Company |
| 11/18/18 | Goodyear FC | 8 : 1 | Goodrich FC | |
| Illinois | ||||
| 11/10/18 | Scottish American FC (Chi.) | 5 : 2 | Harvey FC | |
| 11/17/18 | Bricklayers & Masons FC | 1 : 0 | Lincoln Park | |
| Third Round | ||||
| 12/21/18 | J & P Coats | 1 : 4 | Fore River FC | |
| 12/22/18 | Bricklayers & Masons | 2 : 0 | Scottish Americans | |
| 12/22/18 | Roses FC | 4 : 3 (aet) |
Detroit FC | |
| 12/22/18 | Goodyear FC | 6 : 1 | Magyar American FC | |
| 12/22/18 | Paterson FC | 2 : 1* | Robins Dry Dock | |
| *Match abandoned at 74th minute due to darkness | ||||
| 12/22/18 | R | Paterson FC | 3 : 1 | Robins Dry Dock |
| 12/29/18 | Scottish American FC | 0 : 2 | New York FC | |
| 1/5/19 | Federal Shipyard | 0 : 0 | Morse Dry Dock | |
| 1/12/19 | R | Federal Shipyard | 3 : 5 (aet) | Morse Dry Dock |
| 12/22/18 |
Bethlehem Steel | w/o | Homestead Steel Works | |
| Homestead withdraw due to World War I enlistments |
||||
| Quarterfinals | ||||
| 2/21/19 | Fore River FC | 0 : 0(aet) | Paterson FC | |
| 3/2/19 | R | Paterson FC | 2 : 1 | Fore River FC |
| 3/1/19 | Bethlehem Steel | 5 : 0 | Goodyear FC | |
| 3/2/19 | New York FC | 0 : 2 | Morse Dry Dock | |
| 3/9/19 | Bricklayers & Masons | 5 : 2 | Roses FC | |
| Semifinals | ||||
| 3/29/19 | Bethlehem Steel | 5 : 0 | Bricklayers & Masons | |
| 3/30/19 | Paterson FC | 4 : 1 | Morse Dry Dock | |
| Final | ||||
| at Athletic Field – Fall River, Massachusetts | ||||
| 4/19/19 | Bethlehem Steel | 2 : 0 | Paterson FC | |
| KEY – w/o – walkover, R – Replay | ||||