The electrochemical behavior of the sila-, germa-, and stannacyclopentadienes (metalloles) was studied by cyclic voltammetry. The oxidation and reduction mechanisms of these heterocyclic compounds were investigated. A new method for generation of tetraphenylgermole dianion involving the electrochemical reduction of the corresponding dichlorogermole is proposed. Electrochemical oxidation of the metallole dianions was first studied taking tetraphenylgermole dianion as an example.