The transition metal-catalyzed asymmetric hydrogenation of carbon–carbon double bonds is recognized as one of the most straightforward methods for the preparation of stereopure compounds. Chiral cyclic motifs have widespread applications in organic synthesis and can also be prepared via this strategy. This review summarizes the recent advances (2016–2023) in the stereoselective metal-catalyzed hydrogenation of cyclic α,β-unsaturated ketones, lactams and lactones since considerable developments in this regard were made. The applications of these methodologies in synthesis are also outlined where relevant.