Dirty-face Derring is described as a "short, wiry man of thirty years with a large, brown birthmark covering most of the left side of his face."
After Pete Girly's betrayal and death, Eight-Fingers Oba became Tawni's first mate, and Derring became second mate. A disagreement started to develop between Tawni and Oba, due to the latter growing tired of the endless, senseless killing, so Derring was attempting to use this to work his way onto Tawni's good side.
Oba left the ship before Tawni fought the Mer-Queen, and Derring was appointed as the new first mate. As she watched the Mer-Queen's floating throne sink into the waves, dead mermaids floating all around her, Tawni remarked that "It's a good thing Oba wasn't here to see this." Misunderstanding her, Derring replied that he never liked that coward either, and that "All I saw was a whimpering..." That was as far as he got before Tawni stabbed him to death.
Derring appears only in Heroes of Might and Magic IV.