Trim off large leaves of broccoli. Remove stalks; break into flowerets, and wash thoroughly. Cook broccoli, uncovered, in boiling salted water for 8 minutes or until crisp-tender. Drain and place in cold water about 5 minutes; remove and drain well.
Cut tomatoes in half; scoop out pulp, leaving shells intact. Reserve pulp for use in other recipes. Invert tomato shells on paper towels, and set aside.
Sauté garlic in olive oil until lightly browned; remove from heat, and stir in broccoli, salt, and pepper. Arrange broccoli in tomato cups. Sprinkle each with cheese.
Place tomato cups in two 9- inch square baking pans. Bake at 300° for 5 minutes or until cheese melts.
Note: 1/2 cup grated Parmesan cheese may be substituted for Cheddar cheese.