Preheat oven to 350°F (175°C). Line a 12-cup muffin tin with cupcake liners.
In a large bowl, whisk together flour, sugar, baking soda, salt, and cocoa powder.
In a separate bowl, whisk together vegetable oil, buttermilk, eggs, vanilla extract, and red food coloring.
Pour the wet ingredients into the dry ingredients and mix until just combined. Do not overmix.
In a small bowl, stir the white vinegar into the milk mixture. Let it sit for a minute, then add it to the batter and gently fold it in.
Divide the batter evenly among the prepared cupcake liners, filling each about two-thirds full.
Bake for 20-25 minutes, or until a wooden skewer inserted into the center of a cupcake comes out clean.
Let the cupcakes cool in the muffin tin for 10 minutes before transferring them to a wire rack to cool completely.
While the cupcakes are cooling, prepare the frosting. In a large bowl, beat together softened cream cheese and butter until smooth.
Gradually add the powdered sugar, beating until well combined and fluffy. Stir in vanilla extract and milk until desired consistency is reached.
To prepare the bloody filling, gently warm the raspberry jam in a small saucepan or microwave until slightly melted and pourable. Stir in corn syrup and a drop of red food coloring until well combined.
Once cupcakes are completely cool, use a small knife or an apple corer to carefully remove a small circle from the center of each cupcake. Be careful not to go all the way through.
Spoon a small amount of the bloody filling into the cavity of each cupcake.
Frost the cupcakes generously with the cream cheese frosting, swirling it to create a dramatic effect.
Insert a decorated toothpick into the top of each cupcake to resemble vampire fangs.
Notes
These cupcakes are best served at room temperature. Store any leftovers in an airtight container.