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How do double Forcefields work on Dreadwing? Will both be scrapped in a single attack thus making 1 pointless? Or will 1 trigger and resolve then the 2nd is left on?

Both Forcefields will try to apply. You’ll need to choose one, which would reduce the damage, making the other Forcefield no longer apply to the scenario.
Source: Wizards of the Coast (2019-04-05)    【Link to Ruling】
Tags: Dreadwing, Sky Destroyer