Cunningham was born at Fernhill House, Glencairn, Belfast, and educated at Belfast Academy and at Merchiston Castle School, Edinburgh. He became a stockbroker with his father, Josias's, firm in Belfast, but also acquired business interests, becoming chairman of The Northern Whig newspaper and the tobacco firm Murray Sons & Co Ltd.
Cunningham was appointed to the Privy Council of Ireland in the 1920 New Year Honours following his membership of the Housing Committee on Finance, entitling him to the style "The Right Honourable". He was elected to the Senate of the Parliament of Northern Ireland on its formation in 1921 and served until 1945.
- Obituary, The Times, 24 August 1946
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