Colobomycter pholeter, a parareptile from the Early Permian of Oklahoma, USA (~289 mya). Although known only from partial skull fossils, its full size was probably around 30cm long (1′).
It had huge fangs at the front of its jaws, along with a few other enlarged teeth further back, all with serrated edges that show it was clearly a predator. What exactly it was feeding on with this unusual tooth arrangement is unknown – but proposed ideas include piercing through hard-shelled arthropods, or stabbing into smaller vertebrate prey.