Football tournament season
The 1939 National Challenge Cup was the annual open cup held by the United States Football Association now known as the Lamar Hunt U.S. Open Cup.
Eastern Division
Western Division
| Round of 16 | | Quarter-finals | | Semi-finals | | Final |
| | | | | | | | | | | | | | |
| November 13 - Detroit | | | | | | | | |
|
| Bolton All-Stars | 0 |
| January 8 - Detroit |
| Chrysler S.C. | 2
| |
| Chrysler | 2 |
| December 11 - Chicago |
| | Manhattan Beer | 4
| |
| Manhattan Beer | 4 |
| | March 12 - Chicago |
| Swedish American | 0
| |
| Manhattan Beer | 3 |
| December 11 - Buffalo |
| | Bartunek Slavia | 2
| |
| Beck's German-American | 0 |
| January 8, 15 | |
| Kodak Park F.C. | 1
| |
| Kodak Park | 1-0 |
| Dec 11,18/Jan 2 - Cleveland |
| | Bartunek Slavia | 1-3
| |
| Shamrock S.C. | 3a |
| | April 2, 9 |
| Bartunek Slavia | 7
| |
| Manhattan Beer | 2-3 |
| December 11 - Homestead |
| | Morgan | 3-1
|
| Curry S.C. | 0 |
| January 8, 15 - Bridgeville | |
| Castle Shannon-Deutsch Sport Club | 3
| |
| German Sport | 1-0 |
| December 11 - Bridgeville |
| | Morgan | 1-5
| |
| Heidelberg S.C. | 1 |
| | March 12 - Pittsburgh |
| Morgan S.C. | 2
| |
| Morgan | 4 |
| December 11 - Chicago |
| | Sparta | 2
| |
| Sparta Garden City | 1 |
| January 8 - Chicago | |
| Olympia A.F.C. | 0
| |
| Sparta | 7 |
| February 12 - St. Louis |
| | Lindell Trust | 1
| |
| Lindell Trust S.C. | 3 |
| |
| Burke S.C. | 1
| |
|
a) aggregate after 3 games
Final
First game
Second game