1. Cut 8 grape tomatoes into quarters. Combine quartered tomatoes, 1/4 cup cucumber, 1/4 cup bell pepper, and 1/4 cup onion in a small bowl; set aside.
2. Combine remaining grape tomatoes, remaining 1 1/4 cups cucumber, remaining 3/4 cup bell pepper, remaining 1/2 cup onion, 2 tablespoons oil, vinegar, 1/2 teaspoon salt, 1/4 teaspoon pepper, garlic cloves, and canned tomatoes in a food processor; pulse until almost smooth or until desired consistency. Refrigerate 25 minutes.
3. Combine remaining 1 tablespoon oil, juice, minced garlic, remaining 1/4 teaspoon pepper, remaining 1/8 teaspoon salt, and shrimp in a medium bowl. Heat a large nonstick skillet over medium-high heat. Add shrimp mixture to pan; cook 3 minutes or until done, stirring occasionally.
4. Place about 1 cup soup into each of 4 bowls. Top each serving with 5 shrimp and 1/4 cup cucumber mixture.