Preheat oven to 350 degrees F. Lightly grease a 9" springform pan with cooking spray; place a parchment round in the bottom of the pan and spray the parchment. Set aside.
Cream together the butter and brown sugar in the bowl of an electric mixer until creamy, about 1 minute. Beat in the eggs, one at a time, beating well after each addition, followed by the molasses and vanilla.
In a medium bowl, whisk together the flour, spices, baking soda, and salt. Add half of the dry ingredients to the bowl, mixing well. Stream in half of the milk, mixing well to blend in. Add in the remaining dry ingredients, beating well, followed by the rest of the milk, beating to combine.
Spread the batter in the prepared pan and bake for 27-35 minutes or until a toothpick inserted near the center comes out clean or with moist, not wet, crumbs. Cool completely.
To make the chai whipped cream, beat the heavy whipping cream and powdered sugar together on HIGH speed for about 5 minutes or until stiff peaks form. Add in the cinnamon, cardamom, ginger, and cloves and beat until incorporated.
Serve the cake with the chai whipped cream on top!