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Preheat oven to 350°. Heat oil in a large skillet over medium heat. Add garlic and red pepper flakes. Stir until garlic is softened, about 30 seconds. Add broccoli rabe; sea-son with salt and pepper. Cook, tossing, until wilted, about 2 minutes; let cool slightly.
Meanwhile, whisk eggs, milk, 2 teaspoons salt, and 1/2 teaspoons pepper in a large bowl to blend. Add broccoli rabe mixture, bread, and 1/2 cup Parmesan; toss to combine. Transfer to a 1-1/2-qt. baking dish. Top with pancetta and remaining 2 tablespoons Parmesan.
Bake pudding until puffed, browned in spots, and set in the center, 45-55 minutes.
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