Preheat oven to 400F. Slice about 1/2-inch of the top of garlic. Arrange garlic in the center of a tin foil rectangle and drizzle with olive oil and season with salt and pepper. Fold edges of foil over garlic and tightly seal to form a packet.
Place foil packet directly on oven rack and roast at 400F 30-35 minutes until garlic is a light golden brown and very soft. Allow roasted garlic to cool slightly, then remove from foil and skins and finely mash into a paste.
Keep oven on and increase heat to 425F. Line a medium sheet pan with parchment paper and set aside.
In a large bowl, combine flour, baking powder, sugar, and salt. Use a pastry cutter or your fingers to work frozen shredded butter and roasted garlic paste into flour mixture until crumbly.
Add shredded cheese, heavy cream, and buttermilk to flour mixture and gently fold until a shaggy dough forms. Turn dough out onto a surface and gently knead several times until dough comes together.
Lightly flour surface and pat dough into a 1-inch thick square. Cut square into 4 pieces using a benchscraper or knife and stack the pieces on top of one another. Use your hands to flatten dough back down to 1 inch and use a 3-inch biscuit cutter to cut out biscuits
Place biscuits in the center of prepared sheet pan so that they are touching each other. Place pan in the freezer for 15 minutes to chill the fats in dough before baking.
Remove biscuits from freezer and brush with additional heavy cream. Bake biscuits at 425F 13-16 minutes until golden brown. Serve warm and enjoy!