Preheat oven to 350 degrees. Line a baking sheet with parchment paper.
Lightly flour a clean work surface. Spread out 1 roll of pie dough and using a rolling pin roll it out to double the size. Using the top edge of a glass (around 3 1/2 inches wide) or a biscuit cutter, cut out circles and place on prepared baking sheet.
Add 1 TBS of diced apple pie filling in center of each pie circle. Leave a 1/4 inch edge around circle.
On same work area, unroll other pie crust (do not roll thin.) Measure out 3 1/2 x 1/4 inch strips. Place two strips over the pie filling on each pie circle. Then place two more strips crossing the other two strips (like a checkerboard. Seal the ends of the strips to the bottom circle.
Brush milk over all of the strips on the pies. Lightly sprinkle sugar over each pie and lightly sprinkle with cinnamon.
Bake in over for 20-30 minutes until crust is golden brown on tops and bottoms.