Line muffin tin with paper liners and drop an Oreo cookie into the bottom of each one. Set aside.
Make chocolate cake batter according to package directions. Pour batter over each cookie, filling to 3/4 way full. Bake according to package directions or until toothpick comes out clean after inserted. Set aside to cool.
For the frosting, whip butters, vanilla and powdered sugar together, slowly drizzling milk in to moisten. Once all the ingredients have come together into a frosting, whip 2 minutes 'til smooth and fluffy. Stir in oreo crumbs. Spread generously over cooled cupcakes.
For the glaze, microwave peanut butter and maple syrup together for 30 seconds or until warmed and thinned out. {You don't want it too hot to melt the frosting.} Drizzle over each cake using a spoon or pour into a squeeze bottle and drizzle. Top with half a cookie and serve.