Whip the heavy whipping cream to soft peaks in a stand mixer. In a separate bowl, combine melted chocolate and sweetened condensed milk. Fold in whipped cream until completely combined.
Using a small spoon, dollop small amounts (about 1/2 tablespoon) of peanut butter cookie dough into ice cream. Fold in until distributed.
Scoop a quarter of mixture into Tupperware container where you'll be keeping the ice cream. Snip the corner of the Ziploc bag filled with chocolate mixture and drizzle over ice cream. Add another quarter of the ice cream mixture and repeat with chocolate drizzle until all ice cream and chocolate is added. Freeze for four hours or until firm. Enjoy!