Preheat the oven to 325°F (163°C). Line a muffin tin with cupcake liners.
In a large bowl, whisk together flour, cocoa powder, baking powder, salt, and baking soda until well combined and no lumps remain.
In the bowl of a stand mixer fitted with the paddle attachment, beat butter and oil together until butter is smooth and creamy. Add the Redpath® Dark Brown Sugar and Redpath® Granulated Sugar. Cream together until light and fluffy; 3 minutes.
Add the egg and yolk and beat until fully combined. Add a third of the dry ingredients. On low speed, mix until just combined. Add half of the wine and all of the vanilla extract. Mix on low speed until just combined. Repeat process with the remaining dry ingredients and wine, ending with the dry ingredients. Scrape down the sides of the bowl after each addition.
Using a trigger-style scoop or ladle, spoon batter into the prepared tin, filling the liners about ¾ full.
Place into the preheated oven and bake for 20 to 25 minutes. Cupcakes are done when a skewer inserted into the centre of a cupcake comes out clean or the tops spring back when gently pressed.
Let the cupcakes cool on a wire cooling rack for 5 to 10 minutes before carefully removing them from the tin and cooling completely on the rack.