Heat 2 tablespoons oil in 10-inch skillet over medium heat until shimmering. Add fennel and cook until slightly softened, about 5 minutes. Stir in garlic and cook until fragrant, about 30 seconds. Stir in tomatoes and continue to cook until tomatoes break down slightly, about 5 minutes. Transfer fennel mixture to medium bowl; stir in remaining 2 tablespoons oil, olives, almonds, vinegar, parsley, sugar, salt, and pepper. Serve warm or at room temperature.

Makes About 2 cups