After completing his legal education, Cunningham opened a law practice in his hometown of
Benton Harbor, Michigan. When the United States entered
World War I in April 1917, Cunningham closed his legal practice and began serving on active duty in the
United States Navy. He served with the rank of lieutenant in the paymaster's department and aboard the . Upon his discharge from the Navy in 1919, he returned to Benton Harbor and resumed his law practice. He served two terms as prosecuting attorney for
Berrien County from 1929 to 1933 and for 23 years from 1933 to 1956 as the city attorney of
Benton Harbor, Michigan. Cunningham was also a noted historian, author and archeologist specializing in Native American artifacts. In 1961, he published "Land of Four Flags: An Early History of the St. Joseph Valley," a history of southwestern Michigan. Cunningham died in 1974 at age 89 and was buried at the Crystal Springs Cemetery in
Benton Harbor, Michigan. ==Head coaching record==