There have been two Baronetcies created for persons with the surname Bailey, both in the Baronetage of the United Kingdom. Both creations are extant as of 2010.

The Bailey Baronetcy, of Glanusk Park in the County of Brecon, was created in the Baronetage of the United Kingdom on 5 July 1852. For more information on this creation, see Baron Glanusk

Baron Glanusk

Baron Glanusk, of Glanusk Park in the County of Brecknock, is a title in the Peerage of the United Kingdom. It was created in 1899 for Sir Joseph Russell Bailey, 2nd Baronet, who had earlier represented Herefordshire and Hereford in the House of Commons as a Conservative. Both his son, the second...

.

The Bailey Baronetcy, of Cradock in the Province of the Cape of Good Hope in the Union of South Africa, was created in the Baronetage of the United Kingdom on 12 February 1919 for the South African diamond magnate and politician Abe Bailey. His eldest son, the second Baronet, married Diana Churchill

Diana Churchill

Diana Spencer-Churchill was the eldest daughter of Sir Winston Churchill and Clementine Churchill, Baroness Spencer-Churchill .- Personal life :...

, eldest child of Winston Churchill

Winston Churchill

Sir Winston Leonard Spencer-Churchill, was a predominantly Conservative British politician and statesman known for his leadership of the United Kingdom during the Second World War. He is widely regarded as one of the greatest wartime leaders of the century and served as Prime Minister twice...

. However, they were divorced in 1935. The second Baronet was succeeded by his half-brother, the third Baronet. He was the son of the first Baronet by his second wife the Honourable Mary Westenra, a famous aviatrix. The third Baronet was also an influential businessman. As of 2010 the title is held by his son, the fourth Baronet, who succeeded in 2009.

Bailey Baronets, of Cradock (1919)

• Sir Abe Bailey, 1st Baronet (1864-1940)

• Sir John Milner Bailey, 2nd Baronet (15 June 1900, East Grimstead
  East Grimstead
  East Grimstead is a village in Grimstead civil parish, on the River Dun in Wiltshire, England, about east of Salisbury.-External links:...
  
   - 13 February 1946, Cape Town
  Cape Town
  Cape Town is the second-most populous city in South Africa, and the provincial capital and primate city of the Western Cape. As the seat of the National Parliament, it is also the legislative capital of the country. It forms part of the City of Cape Town metropolitan municipality...
  
  , South Africa
  South Africa
  The Republic of South Africa is a country in southern Africa. Located at the southern tip of Africa, it is divided into nine provinces, with of coastline on the Atlantic and Indian oceans...
  
  ). Bailey married 12 December 1932 (and divorced 21 August 1935) Diana Churchill
  Diana Churchill
  Diana Spencer-Churchill was the eldest daughter of Sir Winston Churchill and Clementine Churchill, Baroness Spencer-Churchill .- Personal life :...
  
  , daughter of Winston Churchill
  Winston Churchill
  Sir Winston Leonard Spencer-Churchill, was a predominantly Conservative British politician and statesman known for his leadership of the United Kingdom during the Second World War. He is widely regarded as one of the greatest wartime leaders of the century and served as Prime Minister twice...
  
  ; married, secondly, Muriel Serefin Mullins, daughter of James Henry Mullins, 18 October 1939 (divorced 1945); married, thirdly, Stella Mary Chiappini, daughter of Charles Du Plessis Chiappini, 4 May 1945; died without issue.

• Sir Derrick Thomas Louis Bailey, 3rd Baronet (1918-2009)

• Sir John Richard Bailey, 4th Baronet (b. 11 June 1947). Bailey is the son of the 3rd Baronet and Nancy Stormouth Darling. He was educated at Winchester College
  Winchester College
  Winchester College is an independent school for boys in the British public school tradition, situated in Winchester, Hampshire, the former capital of England. It has existed in its present location for over 600 years and claims the longest unbroken history of any school in England...
  
   and Christ's College, Cambridge
  Christ's College, Cambridge
  Christ's College is a constituent college of the University of Cambridge.With a reputation for high academic standards, Christ's College averaged top place in the Tompkins Table from 1980-2000 . In 2011, Christ's was placed sixth.-College history:...
  
  . He married Philippa Jane Pearson Gregory and and has three children.