Preheat oven to 400ºF.
Cut the tip off the head of garlic. Place it in the middle of a piece of foil, drizzle with EVOO and season with salt and freshly ground black pepper. Fold foil up around it then transfer to the oven and roast 40-45 minutes, until the cloves are tender.
After the garlic has been roasting for 20 minutes, place tomatoes onto a baking sheet and toss them in the remaining 2 tablespoons EVOO. Season them with salt and freshly ground black pepper and roast them until they’ve softened and burst open, about 10-15 minutes.
Transfer the roasted tomatoes to a medium-size mixing bowl and let cool slightly. When the garlic has finished roasting, squeeze the softened cloves into the bowl of tomatoes and mash them together.