Pre-heat oven to 350 degrees and line two cupcake tins with cupcake papers.
Combine cocoa powder and chocolate chips in a heat-proof bowl and pour in the boiling water. Let sit for one minute before using a whisk to stir the chocolate until it’s melted and smooth.
In the bowl of a stand mixer or in a large bowl with a hand mixer, cream butter and sugar together until light and fluffy, about 2-3 minutes. Add eggs one at a time and beat until well blended.
In a separate medium bowl combine flour, baking powder, and salt. Slowly add the flour mixture to the butter/sugar mixture and blend until just combined, taking care not to over-mix.
Add half the chocolate mixture and half the wine and blend until just combined. Add the rest of the chocolate and the rest of the wine and blend again until just combined.
Fill cupcake papers about ¾ of the way full (I like to use a cookie scoop to fill). Bake for 20-22 minutes, until a tester inserted into the center of the cupcakes comes out clean.
Let cupcakes cool for a couple minutes in pan before moving to wire racks to cool completely. Frost cupcakes once they're completely cooled. Top with sprinkles if desired.