Many times, actually.
In other worlds, and other places (and of course, in other comics as well!).
So, let’s explore a few of those first meetings!
One of One
Adding More Earths
Back In Time
But, young Bruce Wayne met Superboy once before (as detailed in World’s Finest Comics #84, September-October 1956), but Superboy didn’t know it was Bruce Wayne who prevented crook Thad Linnis (whom young Bruce was working with) from learning Superboy was really Clark Kent! But, Bruce does know and keeps the secret for years!
...preventing him from having too much knowledge of the future, and thus accidentally making it not happen).
Working with Superman had quite the effect on Dick Grayson, as he had taken his name for his future super-self, Nightwing, from Superman….as Superman had become Nightwing, a non-powered crimefighter, when he fought crime in the city of Kandor with Jimmy Olsen being the Kandorian Nightwing’s partner as Flamebird).
Superman and Batman even faced foes that only the two of them could handle, such as the Moon Man, the Composite Superman, Dr. Zodiac, the Weapons Master, the Pantheon and Null and Void.
To save Superman from a kryptonite trap, Batman and Robin work against the Man of Steel, yet on his side, by keeping him away from thugs who have the one substance that could kill him...
...nice to see heroes caring about each others welfare.
In the cartoons, Superman and Batman were just partners (along with Wonder Woman, Aquaman and Robin) in the Super Friends without any first meetings ever being presented. But, in the Superman: Animated Series, on October 4, 1997, is when those characters first met as Batman came to Metropolis to stop the Joker from selling Luthor a kryptonite statue in the episode, “World’s Finest”, written by Alan Burnett and Paul Dini.
The Real First Time