Preheat oven to 400F.
Place a large, oven-safe skillet over medium-high heat with 2 turns of the pan of EVOO, about 2 tablespoons. Season chicken breasts with salt and pepper, and place into the hot skillet. Cook until golden brown on each side, 4-5 minutes, then transfer to the oven to finish cooking, 4-5 minutes more.
While the chicken is working, place a medium skillet over medium heat with 1 turn of the pan of EVOO, about 1 tablespoon. Add the bacon to the pan and cook until golden brown and crispy, 4-5 minutes. Remove the cooked bacon from the pan and reserve.
Add the onion to the same pan and cook until tender, 4-5 minutes. Add the Worcestershire, brown sugar, cider vinegar, maple syrup, orange juice and zest, raisins, brandy or orange liqueur (if using) and cranberry sauce to the pan. Season with salt and pepper and bring up to a simmer. Cook sauce until thickened and raisins have plumped up, 2-3 minutes.
Serve the sauce warm over the chicken breasts with Cider Sweet Potatoes alongside.