Preheat oven to 350°.
Cut zucchini in half lengthwise; scoop out pulp, leaving 1/4-inch-thick shells. Sprinkle shells with salt and pepper; set aside. Coarsely chop pulp.
Heat oil in a medium nonstick skillet; add garlic, and sauté 1 minute. Add squash pulp; cook 11 minutes or until liquid evaporates, stirring occasionally. Remove from heat; stir in stuffing mix, tomato, and Italian seasoning.
Spoon vegetable mixture evenly into zucchini shells. Place in a 13 x 9-inch baking dish coated with cooking spray. Sprinkle evenly with cheese. Bake, uncovered, at 350° for 30 minutes or until zucchini shells are fork-tender.