This miniature, and three others by Hilliard, date from around 1600 and were part of the 'Bosworth Jewel', which commemorated the start of Tudor rule after Henry VII's victory over Richard III at the Battle of Bosworth in 1485. The four portraits show Henry VIII's father, Henry VII, founder of the Tudor dynasty; Henry VIII himself; Queen Jane Seymour; and their son Edward, later Edward VI. The Jewel was intended to show the continuation of the dynasty through Henry VIII to Prince Edward. It was presented to Charles I by Nicholas Hilliard's son. The four miniatures were contained in an enamelled gold box which bore a depiction of the Battle of Bosworth on the lid. The Jewel seems to have been one of the items sold from the collection under Oliver Cromwell and, although the four miniatures had returned to royal ownership in the late seventeenth century, the box was lost. The four miniatures are now in Victorian frames.

Inscribed in gold: Ano Dni: 1509. Aetatis Suae .54.