Process pepperoni slices, bacon, and olives through the fine cutter of a meat grinder.
Stuff pocket of roast with pepperoni mixture; secure opening with wooden picks. Brown beef on all sides in hot oil in a large Dutch oven. Remove beef to a covered roasting pan, reserving pan drippings in Dutch oven. Sauté onion, celery, and green pepper in reserved pan drippings. Add tomato, wine, oregano, bay leaf, salt, and pepper; simmer 5 minutes. Pour sauce over eye of round. Cover and bake at 300° for 2 hours or until roast is tender.
Remove meat from sauce; cool. Wrap tightly in aluminum foil; refrigerate overnight. Refrigerate sauce and vegetables overnight. Remove fat layer from sauce, and discard. Strain sauce through a sieve; discard vegetables and bay leaf. Place sauce and carrots in a medium saucepan; cook over medium heat 10 minutes or until carrots are tender.
Cut roast into 1/8-inch-thick slices, and arrange on an ovenproof serving platter. Cover with aluminum foil. Bake at 300° for 20 minutes. Arrange carrots around beef, and serve with sauce.