To be fair, I believe this is the first time anyone's been killed in the present day in the show itself, instead of in the movies.

And Ash dying twice? I can only think of Movie 1. Unless you're thinking of Ash's and Pikachu's out-of-body experience back in Kanto, which was clearly them just being knocked out. (If they had actually died, would Misty and Brock just uselessly wait for them to wake up?)