Oil and its derivatives contaminate many soils and not only affect their chemical and biological properties but also their geotechnical properties. As oil contamination may deteriorate the functioning of piles, this paper addresses the effects of oil contamination on soil–pile interactions. Axial compressive bearing capacities of two close-ended, instrumented piles were investigated in different oil-contaminated sand using frustum confining vessel. Three different oils (gasoil, crude oil, and used motor oil) at different contamination levels were considered and using some strain gauges, the toe, shaft, and the net total bearing capacity of piles, as well as load distributions along the pile length, were derived. The results show that the presence of oil between soil particles has considerable adverse effects on bearing capacities of model piles, especially the shaft bearing capacity. The oil viscosity and percentage, as well as the contaminated sand bed thickness around the piles, are the most influential parameters. The higher the oil viscosity and oil content, the lower the values of the piles’ bearing capacities in comparison to the uncontaminated sand. With some modifications on the bearing capacity parameters of CFEM method, a good agreement was observed between measured and calculated bearing capacity values.