Preheat oven to 375°F. Toss bread cubes, 3 tablespoons oil, and 2 tablespoons melted butter in large bowl. Spread mixture on large rimmed baking sheet. Bake until bread cubes are golden, stirring occasionally, 20 to 22 minutes. Cool.
Mix wine and raisins in small saucepan; let soak 10 minutes. Boil 2 minutes. Cool.
Stir fennel seeds in small dry skillet over medium heat until fragrant and slightly darker, 2 to 3 minutes. Transfer fennel seeds to plate to cool. Finely grind seeds in mortar with pestle or in spice mill.
Heat 2 tablespoons butter with 3 tablespoons oil in large skillet over medium-high heat. Add fennel bulb, shallots, 1/2 teaspoon coarse salt, and 1/2 teaspoon pepper; sauté until fennel is tender and shallots are pale golden, about 7 minutes. Stir in ground fennel seeds, Speck, lemon peel, and fennel fronds. Stir raisins into fennel mixture; cool. DO AHEAD: Bread cubes and fennel mixture can be made 1 day ahead. Store bread airtight at room temperature. Cover and refrigerate fennel mixture.
Preheat to 375°F. Coat 13 x 9 x 2-inch glass baking dish with 1 tablespoon oil. Toss bread cubes and fennel mixture in large bowl. Add 1 cup broth and eggs; toss until moistened, adding up to 1/4 cup more broth if dry. Transfer stuffing to prepared baking dish. Cover with foil coated lightly with oil, oiled side down. Bake until stuffing is heated through, about 30 minutes. Remove foil; bake uncovered until top is crisp and golden, about 30 minutes.