Organosilanes are important and valuable compounds that have found widespread applications in the fields of organic chemistry, agrochemistry, medicinal chemistry, and materials science. In modern synthetic chemistry, molecules featuring carbon−silicon bonds have attracted considerable interest given that these motifs can be efficiently converted to a wide range of functionalities. Among various approaches, transition-metal-catalyzed C−H silylation has emerged as a powerful tool for the synthesis of silicon-containing functional molecules, which has profoundly accelerated the iteration of organosilicon science. Despite the rapid development of C−H silylation, the enantioselective version of this elegant methodology was not known until 2013. In this review, we aim to summarize recent advances in the area of enantioselective C−H silylation mediated by chiral transition-metal catalysts, organized by the different forms of chirality of the enantioenriched organosilanes. We highlight the great potential of this methodology and intend to inspire further research and applications in this emerging area.