Despite the great diversity of reproductive modes in Chondrichthyes, our understanding of their evolution is still limited. Distinct modes co-occurring within lower taxonomic levels (i.e. species within genera), suggest multiple independent transitions throughout the evolution, and the lack of available information to a wide number of species, indicates a low understanding of the real diversity in the group. In this study, we compiled data on reproductive modes of species included in the available phylogenetic framework, reconstructed ancestral states, evaluated the phylogenetic signal of trait, imputed the modes of extant and fossil species lacking reproductive data, and analyzed the relationship between phenotypic variance, age and diversity among clades. Our analyses support at least the 11 reproductive modes described in the literature. Here, we propose a new classification and renaming of some of the previously recognized modes. The ancestral reconstructions indicates that “short single oviparity” was the ancestral mode, with independent transitions between oviparous/viviparous and lecithotrophic/matrotrophic modes. Although the trait showed a high number of transitions, phylogenetic signal was considered significant for the group. The imputation analyses allowed the estimation the reproductive mode of 481 extant species lacking reproductive data and nine fossil species. Finally, we identified a significant relationship between diversity and phenotypic variation in shark orders. These findings increase our knowledge of the evolution and diversity of reproductive modes in Chondrichthyes, evidencing their complexity and dynamics over time.