The electrochemical reduction of 1,2,3,4-tetraphenyl-1,3-cyclopentadiene and 1,2,3,4,5-pentaphenyl-1,3-cyclopentadiene has been investigated in DMF. At low temperatures (less than or equal to -30 degrees C) and under anhydrous conditions cyclic voltammetry experiments indicate that both substrates are reducible in two successive, chemically reversible, one-electron steps, affording the corresponding radical anions and dianions. More complex voltammetric behaviour is detected at higher temperatures, when the radical anions are protonated by the substrate itself, giving rise, via the so-called 'father-son' self-protonation process, to further reducible compounds generating additional basic intermediates. In exhaustive electrolyses, 1/3 of the starting substrate is converted into dihydroreduction products and 2/3 into its conjugate bases. On the other hand, the quantitative formation of the dihydroreduction products is observed when exhaustive electrolyses are carried out in the presence of phenol, which acts as the proton donor instead of the substrate. Under voltammetric conditions, however, evidence of deprotonation of the substrate by the phenoxide anions thus generated is obtained, indicating the occurrence of an 'indirect father-son' self-protonation process, which takes place since phenol is kinetically more acidic, but thermodynamically less acidic, than the substrate itself. The mechanisms of decay of the radical anions are proposed on the basis of the comparison of experimental and simulated voltammetric data: this approach allowed also the determination of the characteristic kinetic rate constants, some of which are strongly dependent on the structure of the substrate, and of the importance of the homoconjugation reaction involving phenol and phenoxide anion. The stereochemistry of the dihydroreduction process and the voltammetric behaviour of the corresponding products are considered also, even in relation to the voltammetric behaviour of the starting substrates.