I would like clarification on the text of this card. If an icebreaker would break 2 subroutines at once, does "When the Runner breaks a printed subroutine on this ice, they lose 1credit" fire one time or two times?

It fires twice even if you used something like Tycoon to break 2 subroutines at once.

^ What they said

Remember the #Hippo/Cutlery/#Ankusa exception too - the moment you break the last sub with one of those, you trash the ice, which prevents the effect from firing.

On Paperclip it also fires twice. If you Hippo it with Paperclip, it doesn't fire at all.