For a purse of 50 guineas, without training, Painter entered the lists with Shaw, the life-guardsman, at Hounslow Heath, on April 18, 1815. Nothing but true courage could have induced Painter to contend with an opponent so much his superior in every point. Shaw was upwards of six feet in height, and above fifteen stone in weight. Having the advantages, also, of military exercise every day, a good knowledge of pugilistic science, frequent practice with the gloves, and so confident of success, that he had challenged all England. Painter, on the contrary, was a debtor in the Fleet, and had only obtained a day-rule. The odds, in consequence, were two to one on the life-guardsman. Cribb and Oliver seconded Painter. The latter set-to with great gaiety, and the soldier did not appear to have much the best of him, but the length and weight of Shaw ultimately prevailed, and numerous terrible hits were exchanged. It was piteous to view the punishment Painter received, and the game he exhibited astonished every one present. The long arms of Shaw were truly formidable, and he stood over Ned, planting his blows with confidence. Painter received ten knock-down blows in succession; and, although requested to resign the battle, not the slightest chance appearing in his favour, he refused to quit the ring till nature was exhausted. The battle lasted twenty-eight minutes.
At Carter’s benefit, at the Fives Court, on Tuesday, March 11, 1816, Oliver and Painter set-to; the latter boxer was considered to have rather the best of it, and, in one instance, Painter hit Oliver away from him with such violence against the rail of the stage, that it was broken. This circumstance occasioned considerable conversation among the amateurs; and, at a sporting dinner which occurred soon after at Belcher’s, the friends of Painter, in order that he might have a chance to recover his lost laurels, subscribed £100 towards a second combat. It was generally thought that Painter was much improved from frequent practice with Carter, in their sparring tour in various parts of England and Ireland, and it was argued that it was during his “noviciate” he was defeated by Oliver. The following challenge was, in consequence, sent by Painter:—