Chiral recognition is essential for various life activities in living organisms and has important implications for areas, such as asymmetric synthesis, drug production and materials science. Synthetic receptors contribute to the understanding of the stereoselective mechanism as well as facilitate the isolation and enrichment of chiral substrates. Supramolecular macrocycles are widely used in chiral recognition studies due to well-defined cavities and abundant active interaction sites. Several macrocyclic molecules with strong enantioselectivity have recently been reported, which generally have unique cavity features such as endofunctionalization or rigidity, and novel macrocyclic receptors with different cavity structural characters exhibit different chiral mechanisms. This featured review mainly summarizes the strongly enantioselective chiral macrocycles in recent years and reviews the corresponding recognition mechanisms according to the cavity properties, aiming to highlight some potential regularities of the mechanisms behind these cavity-strong chiral recognitions and possible challenges in this field.