The result of the geophysical investigation carried out to access the cause of road failure and remediation measures along Ilesha-Osogbo expressway, Osun State, South-western Nigeria is presented. The study involved integrating the dipole-dipole technique of electrical resistivity method with the ground penetrating radar (GPR) method. Two dipole-dipole traverses, one long and 20 short GPR profiles were established across the failed section of the road. The dipole-dipole data were interpreted using the Diprowin software to produce the pseudo-section while the GPR data were interpreted using the RadProwin to produce the radargram. The result revealed that the failed road exhibit incompetent layer of resistivity values ranging between 17 Ωm to 171 Ωm lying between two competent layers of resistivity values greater than 200 Ωm. A combination of the dipole-dipole technique and the GPR techniques revealed the depth extend to failure to about 4.5 meters to 5 meters deep which overlie a basement rock of undifferentiated gneiss, a rock that is easily prone to weathering. The water level was observed to occur at shallow depth of about 2 meters and infiltrates the entire weathered layer. The shallow groundwater level coupled with the water-logged clayey layer derived from the weathered materials from basement rock were found responsible for the failure of this section of the road. The study recommends the excavation of the waterlogged clayey layer to a depth of about 5 to 6 meters deep into the subsurface and replacement first with heavy boulders of granitic materials and later overlaid with a thick layer of highly resistive landfill materials such as laterite. The result of the two techniques used in this work have proved to be supportive due to the integration of the double dipole technique with the GPR technique, a relatively new technique recently being introduced into road failure mapping.