One day in advance, cut fondant flower, flower center and leaf using largest flower, smallest round and largest leaf Cut-Outs. Attach flower center to flower by brushing lightly with water. Let pieces dry on cornstarch-dusted surface. When completely dry, attach pieces to lollipop stick with melted candy. Set aside.
Bake and cool cupcake in muffin pan without baking cup. Turn cupcake upside down, lightly ice with buttercream and cover with red fondant. Turn cupcake right side up, cut a 3/8 in. strip of fondant and attach to rim of flowerpot with damp brush. Lightly ice top of cupcake and cover with cookie crumbs. Insert flower.