Preheat oven to 400°F.
Cut 4 to 5 slits on one side of the eggplant and place it slit-side-up on a baking sheet. Trim about an inch off the top of the head of garlic, just exposing the tops of the cloves inside. Place the garlic on a piece of aluminum foil, drizzle with a little EVOO, wrap it up and place it in the oven alongside the eggplant. Roast them both for about 30-40 minutes, until the eggplant looks like a flat tire.
When the eggplant and garlic only have about 15 minutes left to roast, put the grape tomatoes on a baking sheet, drizzle them with some EVOO and season with salt and freshly ground black pepper. Transfer to the oven and roast for about 15 minutes.