Preheat Oven to 450º
Trim and chop cauliflower into bite sized florets. Put florets into a gallon zip lock bag, add olive oil, garlic and seasonings and toss until cauliflower is well coated. Pour the cauliflower onto a parchment lined baking sheet and spread out as much as possible. Place in oven and roast for 30-40 minutes or until cauliflower is tender and browned.
While the cauliflower roasts, fry bacon in a tall pot. Remove bacon and drain on paper towel, add onions to the pan and saute until translucent.
When cauliflower is done roasting allow it to cool for 10 minutes. Then add cauliflower, 2 cups sweet corn and chicken stock to your blender/food processor. If your blender or food processor bowl is too small, you will have to do this step in batches. Puree ingredients until smooth.
Pour pureed mixture into your pot with the onions, turn burner to medium high. Add the remaining sweet corn and the whole milk and stir to combine. Allow to simmer for 15 minutes. Then add crumbled bacon and cheese, stirring continually until cheese is melted.
Served topped with shredded cheddar and crumbled bacon.