Combine raisins and Amaretto in a bowl. Microwave at high setting 1 1/2 minutes; drain well.
Combine raisins, apple, sugar, flour, and cinnamon in a bowl. Toss well, and set aside.
Place 1 phyllo sheet on work surface (cover remaining dough to keep from drying); lightly coat with cooking spray. Working with 1 phyllo sheet at a time, coat remaining 7 phyllo sheets with cooking spray, placing one on top of the other. Place a sheet of plastic wrap over phyllo, pressing gently to seal sheets together; discard plastic wrap.
Spoon apple mixture along 1 long edge of phyllo, leaving a 2-inch border. Fold over the short edges of phyllo to cover 1 inches of apple mixture on each end.
Starting at long edge with 2-inch border, roll up jelly-roll fashion. (Do not roll too tight, or strudel may burst.) Place strudel, seam side down, on a jelly-roll pan coated with cooking spray. Score diagonal slits into top of strudel using a sharp knife. Lightly spray strudel with cooking spray.
Bake at 350 degrees F for 35 minutes or until golden brown.