Use your hands to mix flour, sugar, butter, and oats. Mix until they are well-combined and stick together to form small clumps.
Fill cupcake liners 3/4 full with apple cobbler cupcake batter.
Top apple cobbler cupcake batter with crumbs. Be generous with the crumbs. Make small mounds that rise above the tops of the liners.
Top the crumbs with pumpkin pie spice chips (3 or 4 per cupcake). Place the chips toward the centers of the cupcakes; if they are on the edges, they may melt off of the crumbs and onto your cupcake tin.
Bake for 35 minutes or until crumbs begin to brown.