Chiral organometallic half-sandwich complexes with stereogenic metal atoms are close relatives of chiral organic compounds with stereogenic carbon atoms. Similarities and differences between these two classes of compounds are outlined. Some representative metal complexes are discussed in an introductory section followed by a more detailed treatment of the available strategies to control the metal configuration by means of chiral auxiliaries. Special sections are devoted to the discussion of the configurational stability of chiral-at-metal complexes and their applications in stoichiometric and catalytic stereoselective reactions.