Cyriacotheriidae are a family of unusual small-bodied pantodonts known from the Paleocene of the Western Interior of North America. Cyriacotheriids possess a suite of dental characters similar to that of pantodonts (e.g., molar dilambdodonty, lingual molar hypoconulids), as well as several divergent features (e.g., molarized premolars, strong molar conules) that have been interpreted as “dermopteran-like.” The unusual combination of pantodont and dermopteran-like characters, combined with a limited fossil record, has made attempts at understanding the broader relationships of Cyriacotheriidae difficult. This paper reports on a new genus and two new species of cyriacotheriids from the Paleocene of Alberta, Canada, with both species significantly older than those of the only previously described cyriacotheriid, Cyriacotherium. Collectively, the dentitions of these new taxa exhibit derived characters seen in Cyriacotherium (e.g., robust molar conules, strong molar dilambdodonty) in addition to a number of plesiomorphies seen in more basal pantodonts (e.g., conspicuous molar entoconids, deep premolar ectoflexus) and, importantly, posterior premolars that are weakly molariform and non-dilambdodont. A phylogenetic analysis of the new cyriacotheriid, basal pantodonts, dermopterans, and dermopteran-like eutherians resulted in Cyriacotheriidae nesting within a monophyletic Pantodonta. The results strengthen previous hypotheses regarding the pantodont affinities of the family, and suggest that the dermopteran-like features seen in the more derived Cyriacotherium were acquired convergently. Although the discovery of new cyriacotheriids sheds light on the evolutionary history of the family, it cannot resolve the ongoing questions of pantodont origins; nonetheless, their discovery in strata of early Paleocene age indicates that significant parts of the evolutionary history of Cyriacotheriidae, and North American pantodonts more generally, have yet to be discovered.