These first three fossils are scolecodonts. Fossils found in the Kope Formation of Carroll County, Kentucky usually consist of just their jaw remains. These fossils date to the Ordovician Period.
These last three images are of cephalon (front part) of a trilobite (maybe Acidaspis?). The Kope Formation location I was at has quite a lot of larger fragments. See the comb like structure fooled me into thinking they were broken off teeth. I need to be more careful next time!