Looking at how that smooshed down, must not be hardened, or not very much. A hardened tooth would have chipped or broke off, or carriage or apron would have cracked, something. . .Could be the gear for dial is harder, its not a 1:1 ratio, dial gear is smaller, maybe 4:1 I'm guessing.
When you think your done filing, you can probably do a test run in the apron without mounting apron to carriage. Just mount the gear in apron and spin it, to see if you still have a hard spot on the gear below it.
When you do mount apron, move cross feed dial back and forth as you drawl up close with bolts, to get gears meshed.