Cunningham was a teacher with the Women's Missionary Society of the Methodist Church of Canada. She went to Japan in 1887. She worked with a
Japanese Methodist minister and a local official, and became the first principal of the first girls' school in Shizuoka that year. She traveled in Japan, often with other Western women teachers. While in Canada on furloughs, she taught and spoke to Canadian audiences about Japan and her work, with illustrations. She left Japan after her third term of service, during the 1906–1907 academic year. Beginning in 1913, Cunningham was a mission teacher in
Sault Ste. Marie, Ontario, working mainly with European immigrant women and children. ==Personal life and legacy==