Preheat the oven to 350 degrees F. Line a regular-size cupcake pan with 12 cupcake liners.
Combine the flour, granulated sugar, cocoa, baking soda, baking powder, milk, coffee, vegetable oil, vanilla and egg in a large bowl. Beat until smooth. Bake until a wooden pick inserted in the center comes out clean, 18 to 20 minutes. Cool the cupcakes completely.
To assemble: Poke a hole into each cupcake with the handle of a wooden spoon. Fill the cupcakes with about 1 teaspoon Chocolate Bourbon Ganache. Generously frost the top of each cupcake with Chocolate Buttercream Frosting. Place 2 pieces of Pecan Praline Cookie in the top of each cupcake.
Beat the butter in the bowl of an electric mixer fitted with the paddle attachment until light and fluffy. Add the powdered sugar 1 cup at a time until incorporated. Mix in the cocoa. Add the milk and vanilla and beat until light and fluffy. Put the frosting into a pastry bag and cut 1/2-inch off the tip.
Place the semisweet chocolate chips in a heatproof glass bowl. Add the heavy whipping cream, place in the microwave and melt in 30 second intervals until completely melted. Using a hand whisk, whip the melted chocolate and cream until smooth. Add the bourbon. Put the ganache in a pastry bag.
Preheat the oven to 300 degrees F. Place the heavy cream, granulated sugar and butter in a saucepan over medium-high heat and bring to a boil. Remove from the heat and stir in the flour and pecans. Spread the cookie batter onto a parchment-lined cookie sheet and bake until golden brown, 20 to 25 minutes. Remove from the oven and let completely cool. When completely cooled, break into pieces.
This recipe was created by a contestant during a cooking competition. It has not been tested for home use.