Battle of Winceby The Battle of Winceby took place on 11 October 1643 during the English Civil War near the village of Winceby , Lincolnshire about 4 miles ( 6 km ) east of Horncastle . Prelude . During the summer of 1643 , the Royalists laid plans to win the war by marching on London . However , before this could be contemplated , it would be necessary for them to defeat the Parliamentarian forces holding Kingston upon Hull and Plymouth ; otherwise , as the Royalist forces moved on London , the garrisons of those two towns could sortie out and attack the Royalist rear areas . While these sieges were underway , Charles I of England decided to make the best use of his time by reducing Gloucester , the one great fortress of Parliament in the west . Parliamentary forces relieved Gloucester on 5 September . The relieving army was bought to battle by Royalist forces in the First Battle of Newbury ; it was a tactical draw but a strategic victory for the Parliamentarians as it reduced the likelihood of a Royalist attack on London . Meanwhile , the second Royalist siege of Hull had commenced . The Eastern Association forces under the Earl of Manchester promptly moved up into Lincolnshire , the foot besieging King ' s Lynn ( which surrendered on 16 September ) while the horse rode into the northern part of the county to give a hand to the Fairfaxes . Fortunately for the Parliamentary Forces , the sea communications of Kingston upon Hull were open . On 18 September , part of the cavalry in Hull was ferried over to Barton , and the rest under Sir Thomas Fairfax went by sea to Saltfleet a few days later , the whole joining Oliver Cromwell near Spilsby . In return , the old Lord Fairfax , who remained in Hull , received infantry reinforcements and a quantity of ammunition and stores from the Eastern Association . On 9 October Parliamentary forces under Manchester laid siege to Bolingbroke Castle . The battle . On 9 October , Sir John Henderson , the Royalist governor of Newark - on - Trent , took a large body of 1 , 500 men , consisting predominantly of cavalry in 8 troops , with some dragoon s and infantry , to relieve the garrison at Bolingbroke . After a sharp skirmish they took Horncastle from a small outlying detachment of Fairfax ' s force . The Parliamentary detachment reported back to the main army that the Royalists were moving towards them . The next morning leaving enough men to stop the Bolingbroke garrison from launching a sortie , Manchester arrayed his army on Kirkby Hill , overlooking Bolingbroke . Sometime between 12 : 00 and 14 : 00 hours he ordered a general advance towards Horncastle . The Parliamentary horse which moved faster than the infantry met the Royalists advancing in the opposite direction at Winceby . The field of battle was not ideal as the land falls away into sharp gullies on one side , but it was not bad enough to prohibit a battle . The two forces were roughly the same size and composition because , as with the Parliamentarians , the Royalist infantry was not present . The ensuing battle lasted about half an hour . Cromwell feigned a retreat and lured the Royalists from a good defensive position onto flat ground . A small party of Parliamentarians advanced on the Royalists who discharged their weapons at them . Cromwell then led his main body of horse in a charge hoping to press home his charge before the Royalists had time to reload . But dismounted Royalist dragoons managed to fire a second volley , hitting several of the Ironsides . Cromwell had his horse shot from under him , apparently by Sir Ingram Hopton ( who was himself killed in the subsequent fighting and is commemorated by a memorial canvas found above the font in St . Mary ' s Church , Horncastle . The canvas ' inscription describes Cromwell as the ' Arch Rebel ' and bears the incorrect date of October 6 , 1643 for the Battle of Winceby ) , and was only able to rejoin the battle after he had secured another mount . Royalist cavalry under Sir William Savile counterattacked hitting Cromwell ' s right flank . They in turn were attacked in the flank by Fairfax ' s horse . In the resulting melee , the Royalists lost cohesion when the command by Savile to about face was taken to be an order to retreat and Savile ' s horse fled the battle . On the Roundhead ' s left wing the Cavaliers enjoyed greater initial success , but the collapse of the Royalist left and centre meant that Henderson had to retreat or face envelopment . A flanking attack by Cromwell ' s reformed cavalry was enough to cause the Royalists to flee the field in confusion back towards Newark . In Horncastle , at a place now known as " slash hollow " , some Royalists were killed or captured when they became trapped against a parish boundary gate that only opened one way ( against them ) and in their panic the press of men jammed it shut . For the remainder of the day the Roundheads hunted down Cavalier stragglers not stopping until dusk , which in October occurs in early evening , when they were recalled by Manchester . The Royalists lost about 300 men and the Parliamentarians about 20 with a further 60 wounded . On the same day , Newcastle ' s army around Hull , which had suffered terribly from the hardships of continuous siege work , was attacked by the garrison . They were so severely handled that the siege of Hull was given up the next day . Conclusion . Manchester left Bolingbroke Castle under siege and proceeded to retake Lincoln and Gainsborough . With all hope of relief gone the garrison of Bolingbroke Castle surrendered on 14 November . Thus Lincolnshire , which had been almost entirely in the Royalist Earl of Newcastle ' s hands before he was compelled to undertake the siege of Hull , was added , in fact as well as in name , to the Eastern Association .