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Superman & Batman: Generations (1999) #1 - Comic Book DB
Contains two stories:
"1939" -- Superman and Batman first encounter each other at the Metropolis World's Fair to deal with a rampaging robot under the control of the Ultra-Humanite.
"1949" -- Superman and Batman team together to deal with Lex Luthor and the Joker, who have captured Lois Lane in order to draw out Superman.