Pile load tests using Osterberg cells (O-cell) were conducted on cast-in-place concrete piles founded in oil sand fill and in situ oil sand at an industrial plant site in Fort McMurray, Alberta, Canada. Interpreted pile test results show that very high pile shaft resistance (with the Bjerrum-Burland or Beta coefficient of 2.5-4.5) against oil sand could be mobilized at small relative displacements of 2-3% of shaft diameter. Finite element simulations based on linear elastic and elasto-plastic models for oil sand materials were used to analyze the pile load test measurements. Two constitutive models yield comparable top-down load versus pile head displacement curves, but very different behaviour in mobilization of pile shaft and end bearing resistances. The elasto-plastic model produces more consistent matching in both pile shaft and end bearing resistances whereas the linear elastic under- and over-predicts the shaft and end bearing resistances, respectively. The mobilization of high shaft resistance in oil sand under pile load is attributed to the very dense and interlocked structure of oil sand which results in high matrix stiffness, high friction angle, and high shear dilation.