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Preheat oven to 450°. Toss tomatoes, garlic, fennel seeds, and 3 tablespoons oil in a large baking dish; season with salt and pepper.
Roast, stirring occasionally, until the tomatoes are browned and the juices thicken, 30–35 minutes.
Transfer tomato mixture to a large saucepan; add basil, 1 cup torn bread, and 4 cups water. Bring to a boil, reduce heat, and simmer, stirring occasionally and breaking up bread and tomatoes a little, until bread is softened and soup has thickened slightly, 8–10 minutes; season with salt and pepper.
Meanwhile, tear remaining ½ cup bread into smaller pieces; toss on a baking sheet with 3 tablespoons oil; season with salt. Toast, tossing often, until crisp, 5–8 minutes.
Serve soup topped with toasted bread and drizzled with more oil.