New specimens of micromomyid plesiadapiforms recovered from the late Paleocene and early Eocene of the Clarks Fork and Powder River Basins, Wyoming, include previously unknown tooth positions of Chalicomomys antelucanus, the earliest record and first substantial Paleocene sample of Tinimomys graybulliensis, and additional specimens of early Eocene T. graybulliensis, forming the largest known sample (n = 84, MNI = 14) of a micromomyid species from a single fossil locality. These specimens and newly documented intraspecific variability, coupled with the first detailed descriptions of the dentition of Dryomomys szalayi, allow for a systematic revision of the family. Cladistic analysis of the 11 known micromomyid species using 28 morphological characters produced three most-parsimonious cladograms. Results suggest that several Tiffanian taxa previously classified in the genus Micromomys (excluding the type species Micromomys silvercouleei) are more primitive and are referred to a new genus Foxomomys (Foxomomys fremdi, Foxomomys vossae, and Foxomomys gunnelli). Two other Paleocene and early Eocene species previously classified in Micromomys are instead found to share a special relationship with Dryomomys (Dryomomys millennius and Dryomomys willwoodensis) based primarily on the relative size and shape of the premolars. Results further suggest that early Eocene Chalicomomys (monotypic: Chalicomomys antelucanus) is the sister taxon to a clade that includes Dryomomys and Tinimomys, which diverged from each other by the late Tiffanian. The shape of P4 and the relative size of P(3) have distinct patterns of change through the evolution of the group. Additionally, there is a gradual reduction of P2, with Foxomomys having a double-rooted P2, Micromomys, Chalicomomys, and Dryomomys having a single-rooted P2, and Tinimomys lacking a P2. Body size increases from more primitive micromomyids (Foxomomys and Chalicomomys) to more derived genera (Dryomomys and Tinimomys), and size also increases from the older and/or more primitive species within the Dryomomys and Tinimomys lineages.