Preheat the oven to 450 degrees . Loosen the skin of the chicken breast with your fingers and slide the bacon underneath. Season with salt and pepper. Place the chicken, breast side up, in a roasting pan and roast for 30 minutes.
Meanwhile, toss the cauliflower, garlic and oil together in a bowl and season to taste. After the chicken has cooked for 30 minutes, reduce the heat to 400 degrees and add the vegetables to the pan. Roast until the chicken is cooked through and the cauliflower is tender, about 30 minutes. Tent the chicken with foil and let rest for 10 minutes before carving.