Heathcote-Drummond-Willoughby was the second son of Gilbert Heathcote-Drummond-Willoughby, 1st Earl of Ancaster, and his wife Lady Evelyn Elizabeth, daughter of Charles Gordon, 10th Marquess of Huntly. Gilbert Heathcote-Drummond-Willoughby, 2nd Earl of Ancaster, was his elder brother.
He served in South Africa through the Second Boer War 1899-1902; where he was slightly wounded at the Belmont (November 1899). After recovery, he took part in operations in the Orange Free State (February to May 1900), the Transvaal (May to June 1900, July to November 1900) and Cape Colony; and was present at several major battles, including at Poplar Grove and Driefontein (March 1900), Vet River, Zand River, Johannesburg, Pretoria and Diamond Hill (June 1900), Bergendal and Komatipoort (August 1900). Following the end of the war, he returned to the United Kingdom in August 1902.
Heathcote-Drummond-Willoughby entered Parliament for Stamford in the January 1910 general election, a seat he held until 1918 when the constituency was abolished, and then represented Rutland and Stamford from 1918 to 1922.
Heathcote-Drummond-Willoughby married Lady Florence Conyngham, daughter of George Conyngham, 3rd Marquess Conyngham, and widow of Bertram Frankland-Russell-Astley, in 1905. She died in January 1946. Heathcote-Drummond-Willoughby survived her by four years and died in February 1950, aged 77.
- Hart´s Army list, 1903
- "The War - Return of Troops". The Times (36842). London. 9 August 1902. p. 11.
- Hansard 1803–2005: contributions in Parliament by Claud Heathcote-Drummond-Willoughby
|Parliament of the United Kingdom|
Lord John Joicey-Cecil
|Member of Parliament for Stamford
|New constituency||Member of Parliament for Rutland and Stamford
Charles Harvey Dixon
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