 Prior to the battle, Charles had been attempting to link up with the Marquess of Montrose in Scotland following the Royalist defeat in the Battle of Naseby. Although his attempts to do so were unsuccessful, they were disruptive enough that the Committee of Both Kingdoms ordered Sydnam Poyntz to pursue the King with approximately 3,000 horse. After Charles was informed that Chester, his only remaining port, was under siege, he marched there with the intent of relieving the defenders, ordering 3,000 horse under the command of Marmaduke Langdale to camp outside the city while he and 600 others travelled into Chester itself on 23 September 1645. The intent was to attack the besieging Parliamentarians from both sides, Charles mistakenly believing that Poyntz had failed to follow them. In fact he was barely 15 miles (24 km) behind, and moved to attack Langdale's force in the early hours of 24 September. Although Langdale drove Poyntz off, the Parliamentarians besieging Chester sent reinforcements, and Langdale was forced to retreat to Rowton Heath, closer to Chester, and wait for his own reinforcements. This force, under Charles Gerard and Lord Bernard Stewart, was prevented from joining them, and Langdale was instead attacked by both Poyntz's force and the reinforcement. After being driven off the field and failing in an attempt to regroup at Chester itself, the Royalists retreated as dusk fell.
