Preheat your oven to 375 degrees Fahrenheit. Cut the butternut squash in half and scoop out the seeds. Spray them with oil and place them cut-side down on a parchment-covered sheet pan.
Roast the squash halves for 30-40 minutes, or until they are soft and golden. Allow the squash to cool, then scoop out 1 cup of the squash flesh. Reduce the oven temperature to 325 degrees.
Scoop the squash into a large bowl and add the olive oil, honey, vanilla extract and almond extract.
In another bowl, mix together the sugar, flour, almond flour, oat flour, baking soda, baking powder, cinnamon, ginger, cloves and salt.
Slowly add the dry mixture into the wet mixture and whisk together. Whisk the eggs together and whisk them into the batter.
Fold half of the cranberries and chocolate chips into the batter. Grease and line a 9” baking pan and pour the batter into it. Sprinkle the remaining cranberries and chocolate chips on top.
Bake the cake in the oven for 35-45 minutes, or until the cake reaches an internal temperature of 190 degrees with a thermometer.
Allow the cake to cool before removing it from the cake pan. Sift the powdered sugar into a bowl to get rid of any lumps in the sugar. Add the vanilla extract and whisk in the milk 1 teaspoon at a time until it reaches the consistency of your liking. Drizzle the icing on top of the cake and allow the icing to firm up prior to slicing and enjoying.