Preheat oven to 400˚F. Line a large rimmed baking sheet with parchment paper or Silpat.
Slice the whole un-peeled garlic head in half horizontally (parallel with the roots). Peel and slice sweet potatoes into 3/4″ thick pieces.
In a large mixing bowl, combine sliced sweet potatoes, halved garlic head, 2 Tbsp olive oil, 1 Tbsp maple syrup, 1 tsp kosher salt, 1/2 tsp black pepper and toss to combine.
Place in a single layer on prepared baking sheet with the garlic cut-side-up. Bake at 400˚F for 20 min. Remove from oven, stir the sweet potatoes, sprinkle pieces of bacon evenly over the top and bake another 25-30 min or until sweet potatoes are tender and bacon is crisp.