Preheat grill over medium-high heat.
Drizzle the Brussels sprouts stalk with olive oil and place onto grill. Grill for about 10 minutes, turning occasionally to prevent burning. Remove from the grill and allow to cool slightly. Once cooled, cut the Brussels sprouts off the stalk and reserve.
In a large saute pan over medium heat, add the 2 tablespoons olive oil and bacon. Let bacon render, about 3 minutes. Add Brussels sprouts and toss to coat with oil. Add the shallots, garlic, and wine. Cover with a lid and cook until tender, about 3 minutes. Remove from heat and season with salt and pepper, to taste.