Tris(4-fluorophenyl)antimony dicarboxylates (4-FC6H4)3Sb[OC(O)R]2, where R = C10H15 (I) or cyclo-C3H5 (II), have been synthesized by the reaction between tris(4-fluorophenyl)antimony and adamantanecarboxylic or cyclopropanecarboxylic acids in ether in the presence of tert-butyl hydroperoxide with a high yield. The antimony atoms in complexes I and II have a distorted trigonal bipyramidal coordination to the carboxylate ligands in axial positions (OSbO angles are 174.02(10)° (I) and 176.53(5)° (II)). The Sb-O and Sb-Ceqv bond lengths are 2.120(3), 2.121(2), and 2.110(3)-2.117(3) Å (I), 2.147(1), 2.122(1), and 2.120(3)-2.123(2) Å (II). Molecules contain intramolecular contacts between the antimony atom and the carbonyl oxygen atom (2.740(3), 2.867(4) Å (I); 2.694(3), 2.773(4) Å (II)). The structural organization in a crystal of complex I is due to weak intermolecular hydrogen bonds H···F (2.42-2.66 Å). Complex II involves the intermolecular contacts H···F (2.63 Å) and H···O=C (2.50 Å).