Preheat oven to 350°F. If desired, use kitchen scissor to cut scalloped edges on tortillas or to cut into sun shapes. Lightly brush both sides of each tortilla with oil. In a small bowl combine sugar and cinnamon. Sprinkle mixture onto both sides of tortillas.
Lightly press each tortilla into a 10-ounce custard cup or jumbo muffin cup, folding as necessary to fit. Bake for 15 to 18 minutes or until golden brown and crisp. (if necessary, bake tortilla cups in batches.) Cool in custard cups for 5 minutes. Carefully remove from cups; cool completely on wire racks.
To serve, place a scoop of ice cream in each tortilla cup. Drizzle with ice cream topping and top with berries. Serve immediately.