Preheat the oven to 275F. Arrange the tomatoes in a baking dish, then pour the olive oil over top. Add more olive oil as needed so that just the tops of the tomatoes are exposed. Sprinkle with the salt and sugar.
Bake for several hours, stirring every hour or so, until the tomatoes are very dark red. Add more olive oil during the cooking process as needed so the tomatoes don't dry out.
When the tomatoes are cooked, sprinkle the raw garlic over top and cover with plastic wrap. Let sit for at least 20 minutes, then serve as desired.
May be made up to a week in advance and kept in the fridge.
Notes
These are great on crostini, but I love them in marinara, risotto, or just as a topping for fish or chicken. Sky's the limit!