If there is one discernable point where Oliver Cromwell's star emerged from mere cavalry commander to driving force in the New Model Army, the battle of Naseby may be it. Cromwell convinced his commander, Fairfax, to move to an adjacent, more neutral hill, so as to encourage the Royalists to attack. Cromwell was so confident that he wanted to goad the Royalists, especially Prince Rupert, into a fight by giving them a better chance. This level of confidence was not misplaced. Cromwell's actions, as well as the actions of Prince Rupert, were to confirm their reputations. Rupert was the European shock trooper with elan and Cromwell was the disciplined English soldier and stern Puritan. At Naseby, both armies put forward their "A" teams with Prince Rupert, Prince Maurice and the King himself present on the Royal side. Fairfax, Cromwell and Skippon led the Parliamentarian's New Model Army. There would be no denying the superior force after Naseby.

The Battle of Chalgrove is famous mainly because one of Parliament's main political figures, Colonel John Hampden, was wounded in the action and died days later. Hampden was one of the "Five Members" that the King had tried to arrest in Parliament, setting off the war.
The action itself was little more than a skirmish, but brings out the differences between the two armies at this stage of the war. Royalist cavalry commander Prince Rupert was establishing his reputation as a leader of great daring. Rupert was also using newer cavalry tactics that relied on the shock of rapid and decisive action with horse, whereas the Parliamentarians were still relying on firepower and tighter formations with their horse.