The following is list of Challenge Cup Champions:
| Club | Championships |
| Bavarian F.C. | 13 |
| Serbian S.C. | 9 |
| Milwaukee Brewers | 9 |
| United Serbian | 5 |
| Croatian Eagles | 5 |
| Hungarian Tigers | 4 |
| Falk Corp. | 3 |
| F.C. Wacker | 3 |
| Milwaukee Sport Club | 3 |
| Polonia S.C. | 2 |
| Racine S.C. | 2 |
| Vienna S.C. | 2 |
| F.C. Bayern | 1 |
| Lake Shore | 1 |
| Reinders | 1 |
| Neenah Eagles | 1 |
| Year | Club |
| 1935 | Vienna A.C. |
| 1936 | Vienna A.C. |
| 1937 | F.C. Wacker |
| 1938 | F.C. Bayern |
| 1939 | Lake Shore |
| 1940 | Racine S.C. |
| 1941 | N/A |
| 1942 | Falk Corp. |
| 1943 | Falk Corp. |
| 1944 | Falk Corp. |
| 1945 | F.C. Wacker |
| 1946 | F.C. Wacker |
| 1947 | Richard Tigers |
| 1948 | Richard Tigers |
| 1949 | Richard Tigers |
| 1950 | Richard Tigers |
| 1951 | Milwaukee Brewers |
| 1952 | Milwaukee Brewers |
| 1953 | Milwaukee Brewers |
| 1954 | Milwaukee Brewers |
| 1955 | Milwaukee Brewers |
| 1956 | Serbian S.C. |
| 1957 | Serbian S.C. |
| 1958 | Serbian S.C. |
| 1959 | Serbian S.C. |
| 1960 | Bavarian |
| 1961 | Serbian S.C. |
| 1962 | Milwaukee Brewers |
| 1963 | Milwaukee Sport Club |
| 1964 | Milwaukee Brewers |
| 1965 | Bavarian |
| 1966 | Milwaukee Brewers |
| 1967 | Milwaukee Brewers |
| 1968 | Polonia S.C |
| 1969 | Polonia S.C |
| 1970 | United Serbian |
| 1971 | Bavarian |
| 1972 | Bavarian |
| 1973 | Bavarian |
| 1974 | United Serbian |
| 1975 | Bavarian |
| 1976 | Bavarian |
| 1977 | Milwaukee Sport Club |
| 1978 | Serbian S.C. |
| 1979 | Bavarian |
| 1980 | Bavarian |
| 1981 | Bavarian |
| 1982 | United Serbian |
| 1983 | Bavarian |
| 1984 | United Serbian |
| 1985 | United Serbian |
| 1986 | Racine S.C. |
| 1987 | Serbian S.C. |
| 1988 | Bavarian |
| 1989 | Bavarian (U23) |
| 1990 | Reinders |
| 1991 | Neenah Eagles |
| 1992 | Serbian S.C. |
| 1993 | N/A |
| 1994 | N/A |
| 1995 | N/A |
| 1996 | N/A |
| 1997 | Milwaukee Sport Club |
| 1998 | Serbian S.C. |
| 1999 | Croatian Eagles |
| 2000 | Croatian Eagles |
| 2001 | Croatian Eagles |
| 2002 | Croatian Eagles (U23) |
| 2003 | Croatian Eagles |
| 2004 | (Competition no longer exists) |
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