Geotechnical investigation was carried out at two failed segments along Ifon-Benin Highway, with the aim of determining cause, nature, and extent of the road failure. Eight in-situ cone penetration tests was carried out to a depth of about 20 m with a lateral spacing of 20 m. This was complemented by collection of eight soil samples at different depths within the failed segments and analyzed in the laboratory. The laboratory tests conducted were grain size analysis, Atterberg limit test, compaction test, California bearing ratio, undrained uncon ned triaxial test. The failure that existed in both locations are around the embankment, shoulder/edge and wearing course of the highway, due to ingression of water into the subgrade since the earth (natural soil) embankment structure had been eroded by rain water. The laboratory geotechnical results revealed that all the parameters could not meet up with the federal ministry of works and housing speci cation of Nigeria, with plasticity index greater than 20 %, % nes greater than 35 %, CBR values less than 80 % minimum recommended, shear strength parameters; angle of friction and cohesion are less than minimum of 30° and 50 kPa respectively. The CPT revealed predominant sandy silt to clayey silt topsoil and clay substratum with an inferred compressive strength of 20-40 KN/m 2. At both failed segments, the clayey substratum is seriously affected within the upper 6 m. The ingression of water into these foundation structures was due to compromise of the design/construction engineer, since a bridge was supposed to be erected across these two locations. Hence the stream channels across the highway were blocked by the earth-ll embankment. Therefore during wet season, pool of water that supposed to ow across the road through bridge system, continue to dissolve the embankment, and consequently in ltrate into the subgrade. This makes the highway to settle largely under tra c load. In addition, incessant heavy ooding around the embankment/shoulder of the highway might have induced the failure since a bridge was supposed to have been constructed across the two failed segments. This ooded water might have in ltrated into the pavement structural material leading to looseness, and less-cohesion of the layers which invariably reduces subgrade support and weakens various pavement layers.