Early Career
Cunningham was from an Ulster family. His father was Samuel Cunningham, and his elder brothers were Colonel James Glencairn Cunningham, Josias Cunningham stockbroker, Dunlop McCosh Cunningham owner of Murrays tobacco works, Belfast. He was sent to the Royal Belfast Academical Institution, and then to Fettes College in Edinburgh. He then won a place at Clare College, Cambridge - where he was heavy-weight boxing champion.
From 1931 Cunningham went into business in Northern Ireland. He married Dorothy Enid Riley JP on 2 July 1935. Later in the 1930s, Cunningham studied law and was called to the Bar by the Middle Temple in 1939. During the Second World War he served in the Scots Guards although he continued his legal studies, and called to the Bar in Northern Ireland in 1942. He fought the Belfast West byelection in 1943 and the same seat in the 1945 general election.
After the war Cunningham mainly lived in Orpington, although he retained membership of the Ulster Unionist Council. His religious faith led him to be involved with the World Alliance of YMCAs from 1947, and he was Chairman of the National Council of the YMCA in 1949. In 1954 he was elected to Orpington Urban District Council.
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