At Stow on the Wold on 8 May 1645, the royalist field army had split: Goring going towards the West Country to tackle Fairfax; Rupert and the King aiming northwards. Fairfax, however, was ordered to leave the West Country and to make for Oxford, whilst Goring, ordered to rejoin the main field army, failed to do so. On 14 May Fairfax came to Newbury, and on the 19th the New Model laid formal siege to Oxford itself, held by Will Legge, a close friend of Prince Rupert and unlikely to panic. For the time being the King continued northwards, reaching Market Drayton on 22 May, his movement causing the earl of Leven in Yorkshire to try to interpose his Scots between the King's line of march and the successful Montrose in Scotland, thus disrupting parliamentarian efforts in the north. In the King's rear, however, Evesham was taken by forces out of Gloucester garrison under Edward Massey, whilst Fairfax was himself restive and considered his siege operations around Oxford largely pointless.
The royalist commanders, anxious that Oxford should not fall, and uncertain as to its resources, determined to lure Fairfax away by advancing on Leicester. Reinforced by Langdale's Northern Horse, fresh from their triumph at Pontefract, and by men under Henry Hastings from the Midlands, the royalists laid siege to Leicester on 30 May. The governor refused to surrender, although the town was untenable, and the royalists stormed it with considerable slaughter. The Parliament in London was horrified, and issued orders for Fairfax to abandon the siege of Oxford and to seek out the royalist field army, but the resolution which had inspired the Leicester march had dissipated. Prince Rupert wanted to avoid a direct relief march towards Oxford, opting for a march northwards in the expectation that this would force Fairfax to leave Oxford without coming to an unnecessary battle, but on this occasion the King thought otherwise and the royalist army re-supplied itself before moving south. On 4 June, the Northern Horse under Langdale were on the point of mutiny over the decision, and the royalist commanders began to hesitate again.
On 5 June Fairfax left Oxford and rendezvoused at Newport Pagnell with reinforcements. On the 8th, it was resolved to bring the King to battle, and on the 10th Cromwell was appointed Fairfax's lieutenant-general, replacing Vermuyden. It appears that the King anticipated the coming confrontation, to be faced despite a depleted army, but the growing gulf between Prince Rupert and the King's civilian advisers, plus the absence of Goring in the West Country, created tension in the royalist command. Whilst the royal army lay near Daventry, Fairfax marched to Kislingbury on 12 June and his approach took the royalists completely by surprise. The parliamentarian army numbered at least 13,000, whilst the King's numbered somewhere between 9,000 and 10,000, probably nearer the former, and withdrawal was decided upon. The royalists fell back towards Market Harborough, but Fairfax pursued, entering Guilsborough and Naseby townships and coming so close that by midnight on 13/14 June, a council of war was called by the King to prepare for action. Talk of further withdrawal was stilled. They would fight it out. The royalist terrain was advantageous, on a ridge between Oxendon and East Farndon cutting Fairfax off from Market Harborough. Sir Thomas Fairfax, at daybreak on the 14th, had no certainty that the royalists were still in the vicinity, and
he probably expected them to withdraw. The New Model began to concentrate around Naseby. The royalists, poorly served by their scouts, had no inkling of Fairfax's movements, and Rupert himself went out to reconnoitre. His observations led the royalists to abandon their defensive position and to seek battle.
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