In this contribution, the first amidinate and amidine derivatives ofp-carborane are described. Double lithiation ofp-carborane (1) withn-butyllithium followed by treatment with 1,3-diorganocarbodiimides, R–N=C=N–R (R =iPr, Cy (= cyclohexyl)), in DME or THF afforded the newp-carboranylamidinate saltsp-C2H10B10[C(NiPr)2Li(DME)]2(2) andp-C2H10B10[C(NCy)2Li(THF)2]2(3). Subsequent treatment of2and3with 2 equiv. of chlorotrimethylsilane (Me3SiCl) provided the silylated neutral bis(amidine) derivativesp-C2H10B10[C{iPrN(SiMe3)}(=NiPr)]2(4) andp-C2H10B10[C{CyN(SiMe3)}(=NCy)]2(5). The new compounds3and4have been structurally characterized by single-crystal X-ray diffraction. The lithium carboranylamidinate3comprises a rare trigonal planar coordination geometry around the lithium ions.