Preheat a grill to medium-high. Divide the pizza dough and form into 2 balls. Place in a large bowl greased with 1 tablespoon olive oil, cover with plastic wrap and let rest at room temperature for 15 minutes.
Meanwhile, in a large skillet, cook the beef over medium heat, breaking up the meat, until browned, about 5 minutes. Drain and transfer to a large bowl.
In the same skillet, cook the bacon until crisp. Transfer to paper towels to drain. Reserve the drippings in the skillet. Add the onion and cook over medium heat, stirring occasionally, until softened, about 5 minutes; add to the beef. Crumble the bacon into the beef mixture and stir in the cheese; season with salt.
On a lightly floured surface, roll out 1 ball of dough into a 12-inch round and transfer to a large oiled baking sheet. Place half the beef mixture on one side of the round. Top with half the tomatoes. Fold over the dough to form a half moon; crimp the edge to seal. Repeat with the remaining dough. Brush the calzones with olive oil. Pierce a vent in the top of each calzone. Transfer the baking sheet to the grill, cover and bake until golden-brown, about 20 minutes.