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1
Heat a skillet over medium-high heat and add the olive oil. Add onions, celery, and fennel and saute until soft and translucent, 4-6 minutes. Add garlic and crushed pepper and cook until garlic becomes fragrant, 1-2 minutes.
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2
Deglaze with Marsala, and allow alcohol to alight, continuing to shake pan until flame subsides and alcohol is burned off. Remove mixture to large mixing bowl.
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3
Add oregano, half the parsley, pine nuts, raisins, bread crumbs, Romano cheese, and salt and pepper to taste. Mix well until all ingredients are incorporated. Taste for seasoning and adjust if necessary.
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4
Begin stuffing the calamari tubes by squeezing a small amount of stuffing in your hand into a cylindrical shape and inserting it into the tube. Be sure not to over-stuff the tubes, or they may burst during cooking. There should be no stuffing at either ends of the tube, only in the middle. Once stuffed, use toothpicks to close tubes.
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5
To cook calamari, heat a large skillet with oil over high heat, and once smoking, add calamari tubes to pan and sear. When they've begun to brown, flip and brown other side. Transfer seared tubes to a pot of simmering tomato sauce, and cook for at least another half hour.
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6
To serve, remove calamari from sauce, remove tooth picks and spoon some tomato sauce over top. Garnish with fresh grated Romano and chopped parsley.
