Since they are seeking to invalidate the patents, I am rooting for Oracle in this suit.

There doesn't appear to be any evidence Kissinger said that. And anyway, they kind of did both lose.

Is it just me or does that sentence mean that both can only win?

Are you sure it is not: "It's too bad they can't both lose."

You are correct, but English is not as strict as math. You can read it as "It's too bad"->"It's not possible" "they both"->"for both of them" "can't lose."->"to loose".