The devil lost on purpose.
As the only judge, he clearly could have decided his own solo was superior. But by letting Johnny win, he feeds into Johnny's cardinal sin (pride). By giving Johnny the golden fiddle, he feeds into the man's pride (which is already at such a level that he'll take a bet with the devil while admitting that the bet itself might be sinful) and lead him on a path to hell more surely than if Johnny had lost the bet.
As the only judge, he clearly could have decided his own solo was superior. But by letting Johnny win, he feeds into Johnny's cardinal sin (pride). By giving Johnny the golden fiddle, he feeds into the man's pride (which is already at such a level that he'll take a bet with the devil while admitting that the bet itself might be sinful) and lead him on a path to hell more surely than if Johnny had lost the bet.
Had Johnny been defeated, he'd have been convinced that he was hell bound and would start looking for salvation. Now that he's been given a hollow victory and a gold trophy, he might get arrogant enough to think he's guaranteed a spot in heaven. Such thinking makes it easier to go down the path of sin and denial.
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