period
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- Ex Provost Milloy, Provost of Rothesay (1893–1896)
- The Right Honourable Sir Winston Churchill (1874–1965), KG, OM, CH, MP, Chancellor (1929–1965)
- Sir Arthur Stanley
- C. J. Bowen Cooke, London and North Western Railway
- How Sir Galahad, Sir Bors and Sir Percival Were Fed with the Sanc Grael; But Sir Percival's Sister Died By the Way
- Richard Hill Dawe, Solicitor to the Great Northern Railway
- Sir Arthur Munro Sutherland (1867–1953), Bt, Chairman and Deputy Chairman of the Royal Grammar School
- Sir Winston Leonard Spencer Churchill (1874–1965), KG, DL, OM, CH, PC, MP
- Sir John Richmond (1869–1963)
- Sir Winston Churchill (1874–1965)
- Mervyn Kersteman King (1845–1934), Master (1874)
- Randolph Churchill (1911–1968), under the Pergola
- Mervyn Kersteman King, Master
- Freedom of the City of Westminster Given to Winston Churchill
- Winston Churchill (1874–1965)
- Sir Lionel Henry Cust
- General Sir David Baird (1757–1829), Soldier (study for Sir David Baird Discovering the Body of Tippoo Sahib)
- Sir Evan Spicer (1849–1937)
- Sir Charles Wright (1876–1950)
- Henry James (1843 1916) (copy after John Sargent)
other
- View of Lake Geneva, Switzerland (C.397)
- Sir Winston Churchill (1874-1965)
- Opening of the Lord Duveen Annexe to the National Portrait Gallery
- Study for 'Breakfast at Chartwell II' (Sir Winston Churchill, 1874–1965, and Clementine Ogilvy Hozier, 1885–1977, Lady Churchill, in the Dining Room at Chartwell, with Their Cat 'Tango')