De Montfort marched east from Hereford on the 2nd August. He crossed the Severn to the south of the heavily fortified city of Worcester, which Edward controlled. He may have used the bridge at Upton, 9 miles to the south, as later armies would do in comparable situations. However Cox has suggested that de Montfort used a ferry at Clevelode, 4 miles closer to Worcester. That night de Montfort quartered at Kempsey, just 4 miles south of the city, presumably intending to challenge Edward, once his son’s army arrived. But Edward had already taken the initiative, marching for Kenilworth on the night of the 1st August, having first feigned a march north towards Shrewsbury with his infantry and baggage. It was probably only the cavalry which rode the 30 miles to Kenilworth. The surprise attack early on the morning of the 2nd caught part of the rebel army encamped outside the castle. Although de Montfort’s son escaped to the castle, still retaining a proportion of his army, Edward had turned the tables. Immediately Edward returned to Worcester to deal with de Montfort.

On the 3rd, or possibly as late as the 4th August, once he had the news of his son’s defeat, de Montfort marched east, intending to unite with his son’s remaining forces. He may have crossed the Avon at Pershore, putting the river between himself and Edward, who was already probably shadowing the rebel army, marching on the road on the north side of the river. De Montfort probably reached Evesham on the morning of the 4th, while his son was en route for Alcester, intending to approach Evesham from the north.

What happened next is subject to considerable dispute, deriving from the original accounts, especially that of Mathew Paris. This suggest that Edward crossed the Avon and closed the route to Kenilworth and then that the three divisions, of Edward, Clare and Mortimer, approach from three directions encircling de Montfort. This has been long interpreted as a manoeuvre to encircle the town and has led to varied scenarios being described by authors for the late 19th century onwards. According to Prothero, Ramsay, Burne and others, Edward divided his forces and encompassed Evesham in three separate division. They argue that he blocked the way to Kenilworth at Clive, identified as Cleeve Prior some miles to the north east of the town. Then Clare and Edward approached from the north to close the Alcester route, while Mortimer advanced on the east side of the Avon to block the bridge from Evesham at Bengeford.  Carpenter, in 1987, following the interpretation of  Pearson and Oman, differed only in suggesting that Mortimer advanced from the west to Bengeworth.

Burne argued that this division of forces was an exceptional and bold strategy with little parallel in medieval warfare; a sign of the brilliance of Edward as a military commander. Cox has argued, very convincingly, that in fact no such division of forces took place and that the chronicles have been misinterpreted. He has suggested that Edward’s whole army approached the battlefield along the Worcester road and deployed close to a place called Siveldston, which he identifies as Siflaed’s stone, on the east side of Greenhill, beside the Salt Street to Offenham bridge. The march via Cleeve and the blocking of Evesham bridge are both dismissed. Carpenter had countered the arguments, but now Cox’s interpretation would appear to have received dramatic support from the recent discovery of a new account, published by Labordiere et al, which shows that Edward’s forces assembled at Mosham Meadow, between the Avon and the Worcester road, and then marched on Evesham.

De Montfort appears to have posted lookouts in the tower of the Abbey church in Evesham and his barber, Nicholas, an expert in heraldry, recognised the banners of the advancing troops as those of de Montfort’s son. But it soon became plain that this had been a ruse by Prince Edward, who had displayed the banners captured at Kenilworth. Even when de Montfort realised the truth he would not take the opportunity to flee, instead choosing to ride out and confront the enemy, despite being heavily outnumbered. His last hope was that his son’s army would arrive to turn the tables, but in fact they were still miles away, en route via Alcester. Unless he had been wholly decieved by Edward's ruse, it is difficult to understand why de Montfort did not attempt some delaying tactic to give his son time to reach the field before he engaged.