Drilling with prestressed concrete (DPC) pipe pile is a nonsqueezing pile sinking technology, employing drilling, simultaneous pile sinking, a pipe pile protection wall, and pile side grouting. The unloading induced by drilling, the pipe pile supporting effect, and the dissipation of the negative excess pore-water pressure after pile sinking, all of which have significant effects on the recovery of soil pressure on the pile side, are the main concerns of this study, which aim to establish a method to reasonably evaluate the timing selection of pile side grouting. The theoretical solutions for characterizing the unloading and dissipation of the negative excess pore-water pressure are presented based on the cylindrical cavity contraction model and the separated variable method. By inverse-analyzing the measured initial pore pressure change data from borehole unloading, initial soil pressures on the pile side of each soil layer are determined using the presented theoretical solutions. Then, the presented theoretical solutions were verified through a comparative analysis with the corresponding measured results. Moreover, by introducing time-dependent coefficients αt1 and αt2 to characterize the pore pressure dissipation and rheology effects, the effects of the negative excess pore-water pressure dissipation on the pile-side soil pressure recovery are discussed in detail.