1. Preheat the oven to 325 degrees F
2. Cut about 1/2-inch off top of garlic head. Trim root, so garlic sits flat. Remove outer layers of papery skin, leaving enough so cloves remain intact.
3. Place garlic into a small baking dish, drizzle olive oil on top, and cover with a lid or aluminum foil.
4. Roast garlic in the preheated oven until cloves are soft and fragrant, about 1 hour.
5. Stir brown sugar, pineapple juice, water, teriyaki sauce, and soy sauce together in a saucepan and bring to a boil; reduce heat to low and keep at a simmer.
6. Squeeze sides of garlic until pasty roasted garlic emerges.
7. Measure 2 teaspoons roasted garlic into the saucepan and whisk until incorporated. Reserve remaining roasted garlic for another use.
8. Stir lemon juice, onion, bourbon whiskey, pineapple, and cayenne pepper into sauce. Bring to a simmer and cook until liquid reduces by half and turns thick and syrup-like, 40 to 50 minutes.
Tip: When grilling, be sure to apply the sauce just before taking the meat off the flame; the sauce has a lot of sugar and can quickly burn. Don't forget to serve extra sauce on the side.
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