OLD SCHOOL: CAPTAIN AMERICA

Captain America, first appeared in Captain America Comics #1 (March 1941) and was created by Joe Simon and Jack Kirby.

OLD SCHOOL: SUPERMAN V FLASH

OK I didn't strictly do this for Old School but what the hey...

OLD SCHOOL: SKYMAN

Created by writer Gardner Fox and artist Ogden Whitney, the character first appeared in the Columbia Comics omnibus title Big Shot Comics #1 (May 1940).