Preheat oven to 450 degrees. Turn a large baking sheet upside down; rub with oil. Place tomatoes, garlic, and 1 tablespoon oil in a food processor; season with salt and pepper. Pulse 3 to 4 times until ingredients are incorporated but chunky.
On a lightly floured work surface, use a rolling pin and your hands to roll and stretch dough until large enough to cover the surface of the baking sheet. (If dough becomes too elastic, let it rest a few minutes.) Transfer to prepared baking sheet.
Spread tomato sauce evenly over dough, leaving a 1-inch border all around. Top with cheese and pine nuts; season with salt and pepper.
Bake until crust is golden, 15 to 20 minutes. Toss arugula with vinegar and 1 tablespoon oil; season with salt and pepper. Sprinkle arugula and olives over pizza.