1st time: Goku fights him on Namek. Still doesn't die
2nd time: Trunks fights him on Earth. Finally dies.
3rd time: Ressurection F.
4th time: Brough back for the multiverse tournament. I guess he's technically not the villain here because he is on Uneverse 7's side, but we know he still has evil intentions once it's all over, and they're probably going to have to fight him again.
There was also that time he was in GT with Cell in Hell, and they fought Goku again when he was in kid form.