Prepare and bake pre-made pie crusts according to package instructions. Allow crusts to cool completely before filling them.
In a bowl, add the pumpkin puree, evaporated milk, instant vanilla pudding, powdered sugar, and vanilla extract and whisk to combine. Once completely mixed, separate half of the mixture into a second bowl.
Add in the pumpkin pie spice to one bowl of pumpkin mixture, and the cocoa powder to the other bowl and mix each to combine.
Whip the heavy whipping cream on medium speed until it forms stiff peaks, about 3-4 minutes. Add half of the whipped cream into the pumpkin mixture bowl and half into the chocolate mixture bowl. Gently fold each until completely combined.
Scoop alternating scoops of pumpkin and chocolate pie filling into the baked and cooled crusts. Once both pies are filled, carefully drag a butter knife through the filling to create a swirled pattern.
Allow pies to chill in the fridge for at least 3-4 hours or until set.