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:—
“Castle Tavern, Holborn, March 21, 1817.
“E. Painter’s compliments to Mr. T. Oliver, and challenges him to fight, on Thursday, the 22nd day of May next, in a twenty-four feet ring, half-minute time between each round, a fair stand-up fight, for one hundred guineas a-side. The place to be appointed by and stakes deposited with Mr. Jackson, who, Mr. Painter understands, is willing to contribute a purse of twenty-five guineas to make up the one hundred. An early answer is requested.”
The following answer was returned:—
“Tom Oliver, with compliments to Mr. Painter, informs him he has received his most welcome challenge to fight him. Oliver certainly cannot refuse to fight him on the day appointed, but requests it to be understood, he will not fight for a smaller stake than £100 a-side, independent of the purse which may be thought proper to be given by the Club.
“Oliver also begs leave to inform Mr. Painter, he agrees to his own proposal, that is, to make it a stand-up fight, in a twenty-four feet ring, at half-minute time between each round; and also the place to be appointed by Mr. Jackson; and, if it meets his pleasure (which it does his most unexceptionably) to deposit the whole stakes in his hands. Your early answer to the above terms is requested, in order that he may apprise his friends to come and make a deposit. They will either meet you at my house, or he will meet you and them at Mr. Thomas Belcher’s, in Holborn, at his.”
“Peter P. Weston—22nd March, 1817.”
“Mr. Painter has to inform Mr. Oliver, that having waited upon Mr. Jackson with the above reply, it is contrary to the rules of the Pugilistic Club to give a purse of twenty-five guineas when the battle-money amounts to £100.
“Castle Tavern, March 24, 1817.”