Preheat oven to 400 degrees. Peel a whole head of garlic. Place cloves in a small oven safe dish and drizzle with olive oil. Roast for 30 to 40 minutes or until soft and golden brown. ( Garlic can also be roasted in a foil packet)
While garlic is roasting a tomatoes and tomato paste to a large crook pot at least 5 quart. Add all remaining ingredients except heavy cream and Romano cheese. Stir well until uniformly combined
Add garlic once it's done roasting and cook on high for 3 hours
Reduce heat to low an puree mixture until completely smooth with a hand blender. Add heavy cream and let simmer another 30 minutes.