As harsh reductive conditions are required to generate metallocene anions, inert spectator cations are a necessity. Thus far, alkali metal cations have been the sole choice, as their reduction potentials surpass those of the corresponding metallocene anions. In principle, other cations could also be suitable, given that their reduction potential transcends that of the corresponding metallocene anion. While this has never been realized, the substantial effect of Cp substitution patterns on the redox properties of metallocenes could principally allow metallocene cations and anions to coexist in one compound. As decamethylcobaltocenium [Co(C5(CH3)5)2] + has one of the lowest reduction potentials (E = -1.94 V, in CH2Cl2 vs Fc + /Fc) of a metallocene cation, the corresponding metallocene anion must exceed this reduction potential sufficiently to prevent decomposition by electron transfer resulting in two neutral metallocenes. While not yet investigated in this context, the introduction of fluorinated electron withdrawing substituents into the Cp scaffold offers a novel approach towards isolating metallocene anions with dramatically increased redox potentials. This has been demonstrated exemplarily for ferrocenes, whereby the addition of every fluorine substituent increases the redox potential by E1/2 = +0.14 V (in CH2Cl2 vs. Fc + /Fc), with the oxidation of pentafluoroferrocene [Fe(C5H5)(C5F5)] occurring at E1/2 = +0.82 V (in CH2Cl2 vs. Fc + /Fc). This effect is substantially more pronounced for trifluoromethyl groups (CF3) due to the absence of conjugated donor effects, with two CF3 substituents increasing the redox potential by a staggering E1/2 = +0.64 V (in CH2Cl2 vs. Fc). Additionally, CF3 groups also offer a greater steric shielding compared to fluorine substituents.