Parliament's Eastern Association army was besieging the royalist garrison at Old Bolingbroke when they were alerted, by a cavalry skirmish at Horncastle on the night of the 10th October, to the threat of a royalist force sent to relieve the garrison.

In response the Earl of Manchester drew up his forces on the morning of the 11th on Bolingbroke Hill, along the road towards Horncastle just above the village. At about 12:00 noon news came in that the royalists were advancing in strength about three miles away. Immediately the parliamentarian horse marched forward about 1.5 miles and deployed, at Winceby. The infantry, under the command of the Earl, but practically commanded by Colonel Sir Miles Hobart, taking longer to form up and much longer in the march than the cavalry, did not arrive on the field until after the royalists had been routed. Had the cavalry action gone badly they would however have provided an important reserve for Cromwell to retreat behind.