In the past decade, selective C-C and C-heteroatom bond construction through palladium-catalyzed direct C-H bond functionalization has been extensively studied by employing a variety of directing groups. Within this category, direct asymmetric C(sp2)-H and C(sp3)-H activation for the construction of highly enantiomerically enriched skeletons still progressed at a slow pace. This minireview briefly introduces the major advances in the field for palladium-catalyzed direct asymmetric C-H bond functionalization via the directing group strategy.