Two isolated cephalopod jaws recovered from the middle Turonian of the Obira area and the Campanian of the Nakagawa area, Hokkaido, Japan, consist of short outer, and large and posteriorly elongated inner “chitinous” lamellae, with a sharply pointed rostrum in the outer lamella. These features are common with the upper jaws of Recent cephalopods. Comparison with the upper jaws of ammonoids and Recent cephalopods indicates that the two Cretaceous upper jaws are attributed to the Coleoidea other than the Octopodida. This assignment is also suggested by the cladistic analysis of the Nakagawa specimen compared with five upper jaw characters on 22 Recent cephalopod species. The Obira specimen differs from the Nakagawa specimen in having a much smaller jaw and a larger jaw angle, but its order-level assignment could not be determined because of imperfect preservation. The Nakagawa specimen shares several common features with the upper jaws of Recent Oegopsina; thus we assigned its higher systematic position to this suborder. Based on the extremely large upper jaw (97 mm maximum length), a new genus and species (Yezoteuthis giganteus) is proposed. This new taxon would have been as large as the modern giant squid Architeuthis, which commonly exceeds more than 5 m in body length. Our study postulates that studies of jaws are important to reconstruct the phylogeny of the Coleoidea.