Blanch the tomatoes in boiling water for about 30 seconds until their skins loosen, then transfer them to an ice bath. Peel off the skins, then roughly chop the tomatoes and set aside.
Preheat your oven to 400°F (200°C). Toss the garlic cloves with a tablespoon of olive oil and spread them on a baking sheet. Roast for about 20 minutes until golden and fragrant.
In a large heavy-bottomed pot, heat the remaining olive oil over medium heat. Add the peeled, roasted garlic and cook for 1-2 minutes until aromatic, filling the kitchen with a warm smell.
Add the chopped tomatoes to the pot. Stir gently and bring to a simmer, encouraging the tomatoes to break down further and release their juices.
Pour in the red wine and stir. Let the mixture simmer gently, uncovered, for about 1 hour, stirring occasionally. The sauce will thicken and deepen in color.
Add salt, black pepper, and sugar (if using) to balance the acidity. Continue simmering for another 30-60 minutes until the sauce reaches your preferred thickness and flavor develops fully.
Taste the sauce and adjust salt or add a pinch more sugar as needed. The finished sauce should be thick, glossy, and fragrant with a deep tomato aroma.
Serve the sauce hot over pasta, or spoon it onto crusty bread for a comforting appetizer. Enjoy its rich, layered flavors and velvety texture.
