To roast tomatoes, preheat oven to 350F. Place tomatoes on lightly oiled baking sheet. Roast 90 minutes, turning after 45 minutes, until very soft and slightly blackened. Once cooled, chop tomatoes and set aside.
Cook pasta as directed on the package. Drain, reserving 1/4 cup of liquid.
In a large nonstick skillet, heat oil over medium heat. Add crushed garlic and cook until slightly golden, 1-2 minutes. Add broccoli raab to skillet; raise heat to high. Cook, tossing constantly, until greens are just wilted, 4-5 minutes. Add tomatoes, cooked pasta, reserved cooking liquid, red wine vinegar and pepper. Toss well. Serve promptly.