Together with the heterosporous lycophytes, the clubmoss family (Lycopodiaceae) is the sister lineage to all other vascular land plants. Given the family’s important position in the land-plant phylogeny, studying the evolutionary history of this group is an important step towards a better understanding of plant evolution. Despite this, little is known about the Lycopodiaceae, and a well-sampled, robust phylogeny of the group is lacking. The goal of this dissertation is to resolve the relationships among evolutionary lineages in the Lycopodiaceae and provide insight into the timing and drivers of diversification in the family. First, to place the evolution of the family within a global and historical context, I generated a densely sampled, time-calibrated phylogeny of the family. I sampled 50% of the estimated 400 extant species in the Lycopodiaceae and used eight fossils to calibrate the age of major divergence events in the family and across the land-plant phylogeny. Further, we used a probabilistic biogeographic model to infer the historical biogeography of the family. Together, these analyses indicate that the Lycopodiaceae originated in the late Devonian, began its early diversification in the Carboniferous, and accumulated much of its extant diversity during the Cenozoic. From a geographical perspective, major cladogenesis events in the family’s history appear to be linked to the breakup of the Pangaean and Gondwanan supercontinents, with long-distance dispersal playing a role in the establishment of younger evolutionary lineages. Second, I examined the drivers of diversification in the species-rich genus Phlegmariurus in the Neotropics. This clade includes an estimated 150 species and is most diverse in high-elevation habitats in the tropical Andes of South America. Using a time-calibrated phylogeny of the group and species distribution and niche data, I demonstrate a strong positive association between lineage diversification rates and the mean elevation of species’ distributions as well as a strong negative correlation between diversification rates and the size of species’ ranges. Further, we employ a paleoelevation-dependent diversification model to test for an association between the uplift of the Andes and diversification in the clade and demonstrate that speciation rates in Neotropical Phlegmariurus are positively associated with increasing elevations in the Andes. Third, I use a phylogenetic framework to test the monophyly of morphology-based species groups in Neotropical Phlegmariurus. I demonstrate that most groups are not monophyletic, and that convergent evolution is widespread in the genus. We use ancestral character-state reconstruction methods for six morphological traits to elucidate patterns of trait evolution and to circumscribe new species groups. A total of eleven new monophyletic species groups are proposed and defined.