Preheat oven to 375F. Stack phyllo sheets on cutting board, spraying each sheet with cooking spray before topping with another sheet.
Cut stack crosswise in half to form 2 dough rectangles.
Mix sugar and cinnamon. Reserve 1 tsp. of the cinnamon mixture. Toss pears with cereal and remaining cinnamon mixture. Spoon half of the pear mixture lengthwise down center of each dough rectangle; fold both long sides of dough over pear mixture to enclose filling, overlapping sides of dough slightly.
Place, seam sides down, on ungreased baking sheet. Spray lightly with cooking spray.