Preheat oven to 375 degrees F (190 degrees C). Spray a baking sheet with cooking spray.
Combine two crescent roll triangles by overlapping the seams, creating a square. Repeat with remaining dough to form 4 squares total.
Spread 1 tablespoon peanut butter in the center of each square; top each with pieces of Asian pear. Sprinkle 1/4 teaspoon cinnamon atop pear slices; top with Cheddar cheese. Fold one corner of a square over to completely cover the fillings, creating a triangle; seal the edges together. Repeat with remaining squares. Arrange pear pockets on the prepared baking sheet.
Bake on the preheated oven until dough is lightly browned, 10 to 15 minutes.