1In 6-quart Dutch oven, heat oil over medium-high heat. Cook garlic and shallots in oil 3 to 4 minutes or until browned. Remove from pan with slotted spoon, reserving oil in pan.
2In small bowl, mix rosemary, salt, pepper and sugar. Rub mixture on all sides of roast. Cook roast in reserved oil until browned on all sides. Add broth and 1 cup of the water. Scatter garlic and shallots around roast. Cover tightly; cook over medium-low heat 1 hour. Turn roast over; cook 1 hour. Turn roast again; cook covered 1 hour longer or until meat is tender, adding squash and figs and turning roast during last 30 minutes.
3Remove roast, fruit and vegetables to platter. Skim fat from broth, if desired. Heat broth to boiling; boil 5 minutes. Stir in port; boil 5 minutes. Shake remaining 1/2 cup water and the flour in tightly covered container; gradually stir into sauce. Heat to boiling, stirring constantly. Boil and stir 1 minute. Serve gravy with pot roast.