Leonardo is a tough fighter, but he is more than a little outmatched by the Crazy Hand. Crazy Hand has a flurry of projectiles on his side like his power balls and missiles. Leonardo can’t cut those in half with his sword or if he does, Leonardo will not escape unscathed. The Crazy Hand has not been around for a while so it is good to see him make a comeback. Crazy Hand wins.
Update 9/28/2019 Leonardo has his Saint Turtle form which is strong enough to turn the tides. This cosmic power can’t be beat. Leonardo wins.