<p>Drilling with a pre-stressed concrete pipe pile is a typical rock-socketed pre-stressed high strength concrete pipe pile with end sealing and side grouting. This paper presents a simplified approach for the nonlinear analysis of the load–settlement response of a rock-socketed pre-stressed high strength concrete pipe pile while considering the effects of end sealing and side grouting. Two models are presented, namely the ultimate base resistance model considering the end sealing effect and the ultimate shaft resistance model considering side grouting. A base load transfer model and a shaft load transfer model are proposed using the present ultimate base resistance and shaft resistance models, reflecting the effects of end sealing and side grouting on the nonlinear response of the pile base and shaft. By considering the progressive deformation of the pile base and shaft, a highly effective iterative computer program was developed by using the proposed load transfer models. The proposed approach was well validated through comparisons with pile–soil interface large-scale direct shear testing, full-size in situ high strain dynamic testing, and full-size in situ static load testing. Our results showed that the proposed approach could accurately estimate the effects of end sealing and side grouting on the load–settlement response of drilling with a pre-stressed concrete pipe piles. The calculated results using the proposed approach were consistent with the corresponding measured results.</p>