He served as the head football coach at the University of Georgia from 1910 to 1919, compiling a record of 43–18–9.
Cunningham was the 14th head football coach at the University of Georgia and brought both continuity and success to the team.
During Cunningham's ten-year tenure as head football coach at Georgia, the Bulldogs only played eight seasons, disbanding the team in 1917 and 1918 as a result of World War I, but his teams produced seven winning seasons, two more than in the first 18 years of the program's history before Cunningham took the reins.
During the hiatus of Georgia football in 1917 and 1918, Cunningham joined the United States Army.
He also served in World War II with the, achieving the rank of colonel.