Following the destruction of King Charles I's main army at the Battle of Naseby on 14 June 1645, the First English Civil War tilted decisively in favour of the Parliamentarians.

The defeat of Goring at the Battle of Langport on 10 July, along with the subsequent "disintegration" of the new troops in South Wales, led to Charles abandoning this plan.

In early August, Charles took 2,500 soldiers and marched north, being forced to turn back at Doncaster by the advance of David Leslie and 4,000 cavalry.

With Bristol now fallen to the Parliamentarians, Chester was the last port under Royalist control, and crucial for its links with recruiting efforts in Ireland and North Wales.

[5] On 20 September 1645, a force of 500 horse, 200 dragoons and 700 foot under the command of Michael Jones attacked the Royalist barricades,[6] and with the defenders completely taken by surprise, they fell back to the inner city.

Both were repulsed, in one case because of the defenders counter-attacking on foot, and in the other because of the inadequate length of the attacker's scaling ladders preventing them from climbing the wall.

After hearing about the situation, Poyntz promised to advance in the morning "with a considerable body of horse",[9] which encouraged the Parliamentarians around Chester to continue resisting.

[11] Langdale advanced northwards with 3,000 cavalry, and at Miller's Heath on the morning of 24 September he became aware of Poyntz's force of 3,000 also moving north.

In addition, Poyntz had underestimated the strength of the Royalists and tried attacking with those troops immediately available, assuming they would be sufficient to charge and destroy the enemy.

[14] The Royalists, while losing fewer soldiers, were now in a precarious position, since reinforcements from Chester were needed to follow up on the success and defeat Poyntz's force.

Shakerley crossed the Dee using a washtub as a makeshift boat, rather than make a detour of 10 mi (16 km) via Holt Bridge,[15] and arrived in Chester and delivered his message after 15 minutes, but no orders were issued for a further six hours after that.

[16] The Parliamentarians, however, did send support: at approximately 2:00 pm, the Chester forces dispatched 350 horse and 400 musketeers under Colonels Michael Jones and John Booth to reinforce Poyntz.

[18] There the retreating cavalry choked up the streets, allowing the Parliamentarian musketeers to fire into the confused mass of horsemen and leading to a rout.

[19] Rowton Heath has been called "a major disaster" for Charles, with casualties estimated at 600 dead and 900 injured, including 50 members of the Life Guard and Lord Bernard.