In a small bowl, whisk together olive oil, red wine vinegar, oregano, salt, and pepper.
Thread 3 cherry tomatoes, 3 slices of pepperoni, 3 mozzarella balls, and 3 olives onto each wooden skewer.
Brush the skewers with the olive oil mixture.
Heat a grill or pan on stove top over medium-high heat.
Grill or sear the skewers for 2-3 minutes per side, until the cheese is melted and lightly charred.
Serve immediately.