Heat olive oil in a large oven-proof skillet, over medium-high heat until oil starts to sizzle; add fennel.
Add garlic to skillet; brown fennel on one side for 4 minutes. Flip carefully and season lightly with salt. Cover skillet with parchment-lined foil and transfer to oven.
Roast until fennel is very tender, 20 to 30 minutes. Let cool slightly.
Increase oven temperature to 430°F . Transfer garlic and fennel in food processor; process until lumpy consistency.
Season with salt and pepper, and stir in 0.70 oz grated parmesan cheese.
Transfer mixture to a smaller baking dish and sprinkle with remaining grated cheese; bake for 20 minutes or until cheese is golden brown.