In the title compounds 4,11-dihydroxy-13-methyl-1,8-di-p-tolyl-2,9-dithia-13- azadispiro[4.1.47.35]tetradecan-6-one, C26H31NO3S2, (I), and 13-benzyl-4,11-dihydroxy-1,8-bis(4-methylphenyl)-2,9-dithia-13-azadispiro[4.1.47.35]tetradecan-6-one, C32H35NO3S2, (II), the piperidine rings adopt distorted chair conformations. The thiophene rings in (I) have envelope conformations, with the spiro C atoms as the flaps. In (II), one thiophene ring (D) has an envelope conformation, with the hydroxy-substituted C atom as the flap, while the other thiophene ring (E) has a twisted conformation on the C—C bond involving the spiro C atom and the toluyl-substituted C atom. In (I), the mean plane of the piperidine ring makes dihedral angles of 75.16 (9) and 73.33 (8)° with the mean planes of the thiophene rings (D and E), respectively. In (II), the corresponding dihedral angles are 70.95 (11) and 77.43 (12)°. In both compounds, there is an intramolecular O—H...O hydrogen bond forming an S(6) ring motif. In the crystal of (I), molecules are linked via O—H...N and C—H...O hydrogen bonds, forming chains along [010]. There are also π–π interactions present involving inversion-related benzene rings, linking the chains to form slabs parallel to (100). In the crystal of (II), molecules are linked via O—H...O hydrogen bonds, forming inversion dimers with an R44(8) ring motif. The dimers are linked by C—H...π interactions, forming slabs parallel to (001).