Im pretty sure Leonardo Sliced through steel footsoldiers all the time so he would own the "man of steel" Plus superman never actually learnt how to fight so leo would kick his arse. Supermans only advantage is flight but leo would quickly cut him down to size with the help of some kriptonite covered ninja stars (Donatello would have done the intel)
Leonardo vs Wolverine. Probably the closest of these three fights. Leos main hope would be to remove wolverines head with his kitanas a throwback to something out of the highlander. No ninja kicks ,punches or throws would work because wolverine would just heal. Strength would probably goto wolverine but because of leos swordsmanship i doubt wolverine would get to use it. skill to leo and intelligence and agility as well, plus leo has experience fighting people with claws. So thats 5-1 Leo, he would out witt wolverine in a long battle but eventually there would be no chracter left for hugh jackman to portray.
