Hey Scott, I have a quick question for you. It's about Dark Dugtrio and Gust
of Wind. If I play GOW while Dark Dugtrio is on the bench(or active) will my
opponent have to flip a coin to see if the pokemon I sent to the bench takes
20 damage? I also would like to know if this power comes into play when you
use attacks such as Pidgey's Whirlwind. Thanks for your time.
-Jared

Dark Dugtrio's Pokemon Power states that the coin flip happens whenever the opponent's active retreats.  The only thing that constitutes retreating is paying the cost in the bottom right hand corner.  Nothing outside of that is retreating.  So, no, Gusting and Whirlwinding will not cause a coin flip.

Scott