From: Superman #132 and Superboy #76 (October 1959)
No Krypto-led stories cover-dated Oct. '59, but he features fairly prominently in one tale, and marginally in another. In the "novel-length" imaginary story from Superman #132, Batman and Robin plug Krypton trading cards into a supercomputer to show Superman what life he would have led had Krypton not blown up. It's mostly Superman gaping as he sees his young alt-self get a haircut or something, but as Jor-El retrieves Krypto from orbit as well, everyone's favorite not-so-super dog is also a part of the family. Or at least, an ugly off-model simulacrum. He's the one who creates a massive accident with science prof Xan-Du's super-static ray:
Accidental? Really? Hm. Both Xan-Du and Krypto get dosed, but unlike the other live specimens run through the experiment, they aren't turned into rainbows and glass baubles. In fact, it doesn't seem to have any effect on them. That night, Kal-El dresses up in a crazy Earth suit for a masked ball...
But when disaster strikes the floating ballroom, Professor Xan-Du, dressed as a superhero called Futuro, springs into action. The MacGuffin Ray has given him powers! And of course, Krypto too!
They become partners, with Kal-El in the Jimmy Olsen role, signal watch and all. When he grows up, Kal-El becomes spaceman and dons the old red-and-blue (the "S" stands for Spaceman!), his parents die in an accident, and Futuro encounters Lois Lane in a rocket sent from Earth and chooses to move there and marry her. But there's one more charge in the Thingamagigathingie, so he zaps Kal-El with it and he becomes Krypton's new defender - Superman. It is unclear whether Futuro brings Krypto with him or if he stays on the planet. Or how a super-computer figured all this out based on a Viewmaster wheel's worth of pictures.
Meanwhile, back in the real world and the past, i.e. Superboy #76's "The Biggest Bully in Smallville!", Clark faces an odd dilemma: How to teach a bully a lesson without revealing he's Superboy. It involves a lot of super-dickery (not a form of bullying, we swear!) like ruining the kid's dinner with X-ray vision, ruining his fishing trip with a displaced whale, and after stealing Clark's carved soap fossils for school...
Krypto pinch-hits by finding actual dinosaur bones which the teacher is quite happy to accept even though that wasn't the assignment. Not sure Clark needed the super-dog to get at them, but there ya go.
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