1. Preheat oven to 400°.
2. Combine port and cherries in a small saucepan over medium heat; bring to a boil. Reduce heat; simmer 4 minutes. Remove from heat; let stand 10 minutes. Drain cherries in a sieve over a bowl, reserving cherries and port.
3. Heat a medium skillet over medium heat. Add 1 tablespoon oil to pan; swirl to coat. Add fennel and onion; cook 10 minutes or until vegetables are almost tender, stirring occasionally. Add garlic; cook 1 minute, stirring frequently. Combine fennel mixture, cherries, and breadcrumbs in a large bowl. Melt 1 tablespoon butter. Drizzle the melted butter and 1/4 cup stock over bread mixture, and toss. Stir in 2 teaspoons chopped sage, chopped thyme, 1/4 teaspoon salt, and 1/4 teaspoon pepper.
4. Cut horizontally through center of pork, cutting to, but not through, other side using a sharp knife; open flat, as you would a book. Place pork between 2 sheets of plastic wrap; pound to an even 1/2-inch thickness using a meat mallet or small, heavy skillet. Brush 1 1/2 teaspoons oil over inside of pork; sprinkle with 1/4 teaspoon salt and 1/4 teaspoon pepper. Spread bread mixture evenly over pork, leaving a 1/2-inch border around outside edges. Roll up pork, jelly-roll fashion, starting with short side. Secure at 2-inch intervals with twine. Brush outside of pork with remaining 1 1/2 teaspoons oil; sprinkle all sides of pork evenly with 3/4 teaspoon salt and 1/2 teaspoon pepper.
5. Heat a large skillet over high heat. Add pork to pan; cook 8 minutes, turning to brown on all sides. Place pork on a roasting rack coated with cooking spray; place rack in a roasting pan. Pour remaining 2 1/4 cups stock in bottom of roasting pan. Roast pork at 400° for 45 minutes or until a thermometer inserted in center of pork registers 138°. Remove pork from pan; let stand 15 minutes. Cut crosswise into 12 slices.
6. Place roasting pan over medium-high heat; add reserved port, thyme sprigs, sage leaves, and shallot; bring to a boil. Cook until liquid is reduced to 1 cup (about 10 minutes). Combine flour and 2 tablespoons water in a small bowl, stirring with a whisk. Add flour mixture to port mixture, stirring with a whisk; cook 5 minutes or until port mixture begins to thicken. Add remaining 1 tablespoon butter, stirring until butter melts. Strain sauce; discard solids. Stir in remaining 1 teaspoon chopped sage, 1/4 teaspoon salt, and 1/4 teaspoon pepper. Serve sauce with pork.
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