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Quarter chicken. Heat oil in 12-inch skillet over medium-high heat. Cook chicken quarters, skin-side down, 3 to 4 minutes or until brown. Remove from pan. Add squash, garlic, salt and pepper to drippings in pan. Cook 2 minutes, stirring occasionally.
Return chicken to pan, skin-side up. Cook, covered, over medium heat for about 10 minutes or until chicken is heated through and squash is tender, adding the tomatoes for the last 2 minutes of cooking. Transfer chicken and squash mixture to a platter and sprinkle with arugula.