| 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 |
