The Roundheads defeat the Cavaliers at the Battle of Maidstone in the Second English Civil War.

Roundheads were the supporters of the Parliament of England during the English Civil War (1642–1651). Also known as Parliamentarians, they fought against King Charles I of England and his supporters, known as the Cavaliers or Royalists, who claimed rule by absolute monarchy and the principle of the divine right of kings. The goal of the Roundheads was to give to Parliament the supreme control over executive administration of England.

The term Cavalier was first used by Roundheads as a term of abuse for the wealthier royalist supporters of Charles I of England and his son Charles II during the English Civil War, the Interregnum, and the Restoration. It was later adopted by the Royalists themselves. Although it referred originally to political and social attitudes and behaviour, of which clothing was a very small part, it has subsequently become strongly identified with the fashionable clothing of the court at the time. Prince Rupert, commander of much of Charles I's cavalry, is often considered to be an archetypal Cavalier.

The Battle of Maidstone was fought in the Second English Civil War and was a victory for the attacking Parliamentarian troops over the defending Royalist forces.

The Second English Civil War took place between February and August 1648 in England and Wales. It forms part of the series of conflicts known collectively as the 1639–1653 Wars of the Three Kingdoms, which include the 1641–1653 Irish Confederate Wars, the 1639–1640 Bishops' Wars, and the 1649–1653 Cromwellian conquest of Ireland.