Application of chiral derivatives of the versatile and ubiquitous cyclopentadienyl ligand has long remained an underdeveloped area in asymmetric catalysis. In this Perspective we highlight recent exciting results that demonstrate their enormous potential. In particular, we provide a comparative analysis of the available ligand families, an overview of their complexation chemistry, and an examination of their application in catalytic enantioselective reactions. We also discuss current limitations and speculate on the developments that are necessary to advance the field further.