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In large bowl, add the heavy whipping cream. Using a stand mixer or hand mixer, beat the cream until stiff peaks form. Set aside.
In a large bowl, add the cream cheese, powdered sugar, vanilla extract and cinnamon. Using a stand mixer or hand mixer beat on medium speed until the mixture is creamy, about 1-2 minutes.
Using a spatula, fold the whipped cream into the cream cheese mixture.
Fill each phyllo cup with some of the mixture. A piping bag with a large tip makes easy work of this. Or fill a large resealable bag and cut a small piece of the corner or a small cookie scoop.
Top each mini cheesecake with a blueberry, raspberry, mini chocolate chips and chocolate shavings. Dust with powdered sugar.
Serve immediately or store in the refrigerator for up to 2 hours.