Borepin, a 7-membered boron-containing heterocycle, has become an emerging molecular platform for the development of new materials and optoelectronics. While neutral borepins are well-established, reduced borepin species have remained elusive. Herein we report the first isolable, crystalline borepin radicals ( 2a , 2b ) and anions ( 3a , 3b ), which have been synthesized by potassium graphite (KC₈) reduction of dibenzo[b,d]borepin in the presence of free cyclic(alkyl)(amino) carbene. Borepin radicals and anions have been characterized by EPR or NMR, elemental analysis, X-ray crystallography and cyclic voltammetry. In addition, the bonding features have been investigated computationally using density functional theory.