Although stagodontid marsupials are among the most distinctive mammals of Late Cretaceous age in North America, there remain significant gaps in knowledge of their dental anatomy, particularly that of the stratigraphically oldest genus, Eodelphis Matthew, 1916. We report here on stagodontid specimens from the Judithian Belly River Group of southeastern Alberta, Canada, that document what was until now previously unknown parts of the upper and lower premolar dentition of Eodelphisbrowni Matthew, 1916 and Eodelphiscutleri (Smith Woodward, 1916). The new information further confirms the distinctiveness of both nominal species of Eodelphis, and bolsters previous hypotheses suggesting a close phylogenetic relationship between E. cutleri and the advanced stagodontid Didelphodon Marsh, 1889. Although the new specimens from Alberta suggest that the problematic holotype of “Boreodonmatutinus” Lambe, 1902 is an upper third premolar, a referral to Eodelphis cannot be made with confidence and the name should continue to be treated as a nomen dubium. Lastly, we report the first occurrence of Didelphodon in strata of the Belly River Group, extending the geological age of the genus into the Judithian, co-eval with species of Eodelphis, and suggesting a significant prior and as yet undiscovered evolutionary history.