Preheat oven to 400˚F.
Line a baking sheet with parchment paper or foil, and set a cooling rack inside the baking sheet. Set aside.
Trim the brussels sprouts, lightly grease them with cooking spray, and season with salt and pepper.
Cut bacon slices in half.
Wrap bacon slices around each sprout; liberally brush each piece with maple syrup.
Arrange brussels sprouts on the cooling rack, bacon seam-side down.
Roast for 25 to 30 minutes, or until bacon is crisp and brussels sprouts are tender.
Remove from oven and let stand 5 minutes.
Meanwhile, combine remaining maple syrup with 1 teaspoon dijon mustard; whisk together until incorporated, taste, and add more mustard, if needed.
Garnish dipping sauce with red pepper flakes.
Serve brussel sprouts with dipping sauce.