Yes, and so can the bushings that support the starter motor armature shaft in the starter motor housing on each end (and the starter drive on the front end) allowing a wobble in the drive. I would inspect the starter bushings and definitely replace the starter drive when you replace the flywheel. Generally if the teeth on one get wore the worn component will eat away at the other rather quickly. New teeth on both would be a smart move and little expense.

Best Regards
Will