Press refrigerated pie crust on bottom and up sides of a square 9-inch tart pan. Bake at 450° for 9 minutes or until pie crust is lightly browned; set aside and let cool.
Cut off pointed end of garlic bulb; place garlic on a piece of aluminum foil, and drizzle with olive oil. Fold foil to seal. Bake garlic at 425° for 30 minutes; cool. Squeeze pulp from garlic cloves into bottom of baked pie crust.
Slice tomatoes, and sprinkle evenly with salt and pepper. Place on folded paper towels, and let stand 10 minutes.
Sprinkle 1/2 cup cheese over the garlic.
Arrange tomato slices over shredded cheese. Sprinkle with remaining cheese.
Bake at 350° for 45 minutes or until tart is lightly browned.