509.4c An ability that reads “Whenever [this creature] becomes blocked, . . .” generally triggers only once each combat for that creature, even if it’s blocked by multiple creatures. It will trigger if that creature becomes blocked by at least one creature declared as a blocker. It will also trigger if that creature becomes blocked by an effect or by a creature that’s put onto the battlefield as a blocker, , but only if the attacking creature was an unblocked creature at that time. (See rule 509.1h.)
So, it will only trigger once, regardless of how many creatures it is blocked by. This means your opponent only needs 1 Stifle.