| First Round | |||||
| Eastern Bracket | |||||
| 2/3/29 | Waterbury (CT) | 1 : 6 | Walsh Chevrolet (Fall River) | ||
| 2/3/29 | Trenton FC | 8 : 1 | Newark Skeeters | ||
| 2/3/29 | Canton FC (Bal.) | 0 : 5 | Bethlehem Steel | ||
| 2/3/29 | New York Hakoah | 7 : 1 | Mamaronek FC | ||
| 2/3/29 | New York Giants | 4 : 1 | IRT Rangers | ||
| 2/3/29 | Rochester Celtic | 3 : 2 | Hungarian SC (Buffalo) | ||
| 2/3/29 | Hungaria Sport Club (NYC) | w/o | First German SC (NYC) | ||
| 2/3/29 | Newark Portuguese | 3 : 0 | Bayonne Rovers | ||
| Western Bracket | |||||
| 12/16/28 | Sparta A & BA (Chi.) | 3 : 0 | Carpenters FC (Chi.) | ||
| 12/16/28 | Madison Kennels (St. L) | 4 : 1 | Ben Miller SC (St. L) | ||
| 12/23/28 | Tablers FC (St.L) | 5 : 2 | Wellston FC (St. L) | ||
| 12/30/28 | Bricklayers FC (Chi.) | 2 : 0 | Buda AA (Ill.) | ||
| 12/23/28 | Wood Hydraulic (Det.) | 1 : 3 | All Scots FC (Det.) | ||
| 12/23/28 | Holley Carburetor (Det.) | 2 : 0 | Flint IMA (Mich.) | ||
| Goodyear FC (Akron) | 4 : 1 | Celtics FC (Cle.) | |||
| 12/23/28 | Thistles FC (Chi.) | 1 : 1 (aet) | Olympia (Chi.) | ||
| R | Thistles FC | W : L | Olympia | ||
| Second Round | |||||
| Eastern Bracket | |||||
| 2/16/29 | Bethlehem Steel | 5 : 0 | Walsh Chevrolet | ||
| 2/17/29 | New York Hakoah | 6 : 0 | Rochester Celtic | ||
| 2/17/29 | Newark Portuguese | 4 : 1 | New York Hungaria | ||
| 2/17/29 | Bricklayers FC | 3 : 1 | Tablers FC | ||
| Western Bracket | |||||
| 2/17/29 | Madison Kennels | 5 : 1 | Thistles FC | ||
| 2/23/29 | Holley Carburetor | 10 : 3 | Goodyear FC | ||
| 2/24/29 | New York Giants | 8 : 0 | Trenton FC | ||
| 2/24/29 | Sparta A & BA | 7 : 0 | All Scots FC | ||
| Quarterfinals | |||||
| 3/3/29 | New York Giants | 2 : 2 | Bethlehem Steel | ||
| 3/9/29 | R | Bethlehem Steel | 2 : 6 | New York Giants | |
| 3/3/29 | Sparta A & BA | 3 : 1 (aet) | Bricklayers FC | ||
| 3/17/29 | New York Hakoah | 3 : 2 | Newark Portuguese | ||
| 3/10/29 | Madison Kennels | 5 : 1 | Holley Carburetor | ||
| Semifinals | |||||
| 3/17/29 | Madison Kennels | 7 : 4 | Sparta A & BA | ||
| 3/24/29 | New York Hakoah | 1 : 0 | New York Giants | ||
| Final | |||||
| First Leg – at Sportsman’s Park – St.Louis, Missouri | |||||
| 3/31/29 | Madison Kennels | 0 : 2 | New York Hakoah | ||
| Second Leg – at Dexter Park – Brooklyn, New York | |||||
| 4/7/29 | New York Hakoah | 3 : 0 | Madison Kennels | ||
| Hakoah All Stars win National Challenge Cup on 5-0 aggregate | |||||
| KEY – w/o – Walkover, R – Replay | |||||