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Preheat oven to 350°. Heat 1 tablespoon oil in an ovenproof pot over medium-high heat. Season chicken with salt and pepper. Cook chicken in batches until browned, 5-6 minutes per side. Transfer to a plate.
Add bacon to pot; cook until rendered. Add carrots, celery, and onion; cook until onion is translucent, 7-8 minutes. Stir in 1 cup wine and tomato paste; simmer for 2-3 minutes. Add remaining 3 cups wine. Boil until wine is reduced by half, 15-20 minutes. Return chicken to pot.
Add broth. Tie thyme and rosemary sprigs together; add to pot. Bring to a boil and cover pot. Transfer pot to oven and braise until chicken is tender, about 1 1/4 hours.
Meanwhile, heat 1 tablespoon oil in a large pot over medium-high heat. Add mushrooms; sauté until browned, about 5 minutes.
Transfer chicken from sauce to pot with mushrooms; keep warm. Simmer sauce over medium heat until reduced by 1/3, about 20 minutes. Season with salt and pepper.
Add mushrooms and chicken to sauce. DO AHEAD Coq au vin can be made 3 days ahead. Chill uncovered until cold. Cover; keep chilled. Rewarm before serving.