When Sir Robert Tailboys was born about 1449, in Kyme, Lincolnshire, England, his father, Sir William Tailboys, was 35 and his mother, Lady Elizabeth Bonville, was 25. He married Elizabeth Heron before 1467. They were the parents of at least 5 sons and 2 daughters. His occupation is listed as sheriff in Lincolnshire, England. He died on 31 January 1494, in his hometown, at the age of 46, and was buried in Kyme, Lincolnshire, England.
Wars of the Roses was a series of English civil wars for control of the throne of England between the royal families House of Lancaster and the House of York. The name of the war was derived as the red rose was the symbol of the Lancastrians and the white rose was the symbol of the Yorks.