Recently, with the boosted development of radical chemistry, enantioselective functionalization of C(sp3)-H bonds via a radical pathway has witnessed a renaissance. In principle, two distinct catalytic modes, distinguished by the steps in which the stereochemistry is determined (the radical formation step or the radical functionalization step), can be devised. This Perspective discusses the state-of-the-art in the area of catalytic enantioselective C(sp3)-H functionalization involving radical intermediates as well as future challenges and opportunities.