Preheat the oven to 375°F and butter a 10-inch pie plate.
Distribute the raspberries in the prepared pie plate and sprinkle with 2 tbsp of the sugar.
In a small bowl, beat together the milk, eggs, amaretto and butter. Add the flour, another 2 tbsp of sugar, baking powder, and salt and beat to a smooth batter. Pour over the raspberries and bake until golden brown and set in the middle, about 30 minutes. The batter will puff slightly.
While the batter is baking, prepare the whipped cream. If using a stand mixer or hand mixer, pour the cream into a large bowl, add the icing sugar and vanilla, and whisk on medium-high speed for about 4 minutes, until medium firm peaks are formed. If using an immersion blender, pour the cream, sugar and vanilla into a 4-cup jar and blend for the same time, until medium peaks are formed. Cover the container with plastic wrap and place in the fridge until ready to use.
When the clafoutis has finished baking, remove it from the oven and sprinkle it with the cinnamon and the remaining 1 tbsp sugar. Let cool for 15 minutes before cutting into wedges. Serve with the whipped cream.