Direct catalytic transformation of C-H bonds to new functionalities has provided a powerful strategy to synthesize complex molecular scaffolds in a straightforward way. Unstinting efforts of the synthetic community have helped to overcome the long-standing major challenge of regioselectivity by introducing the directing group concept. However, the full potential of the strategy cannot be realized unless the activated C-H bonds are stereochemically controlled. The enantioselective C-H bond functionalization could provide an imperative tool for a sustainable way of synthesizing chiral complex molecular scaffolds. Despite the intrinsic challenges in achieving stereocontrol, the synthetic community has developed different tools in order to achieve stereoselective C-H bond functionalization. In this review, we discuss the remarkable recent advances in the emerging area of enantioselective C(sp(2))-H bond functionalization to highlight the challenges and opportunities, emphasizing the different techniques developed so far.