The Arabidopsis DA1 genes appear to have multiple functions in regulating organ size and abiotic stress response, but the biological roles of its closely-related genes remains unknown. Evolutionary analyses might provide some clues to aid in an understanding of their functional diversification. In the present work, we characterized the molecular evolution and expressional diversification of DA1-like genes. Surveying 354 sequenced genomes revealed 142 DA1-like genes only in plants, indicating plant-specificity of these genes. The DA1-like protein modular structure was composed of two UIMs (ubiquitin interaction motifs), one LIM-domain (from lin-11, isl-1 and mec-3), and a conserved C-terminal, and was distinguishable from the already defined three groups of LIM-domain proteins. We further found that the DA1-like genes diverged into Classes I and II at the ancestor of seed plants and acquired thirteen clade-specific residues during their evolutionary history. Moreover, diverse intron size evolution was noted following the transition from size-expandable introns to minimal ones, accompanying the emergence and diversification of angiosperms. Functional diversification as it relates to gene expression was further investigated in soybean. Glycine max DA1 (GmaDA1) genes showed diverse tissues expression patterns during development and had substantially varied abiotic stress response expression. Thus, variations in the coding regions, intron size and gene expression contributed to the functional diversification of this gene family. Our data suggest that the evolution of the DA1-like genes facilitated the development of diverse molecular and functional diversification patterns to accompany the successful radiation of plants into diverse environments during evolution.