Pile jacking is a kind of competitive method for pile installation due to its less noise and vibration pollution. In this paper, the pile jacking process has been numerically simulated by considering the friction fatigue, and the characteristics of sand-pile interface shear paths at different depths were thoroughly investigated. It is found that during the cyclic jacking process, the interface shear path at a specified depth tends to transform from one-way shear to two-way shear, especially for the shallow to middle depth. But for the deep soil layer, one-way cyclic shear is still the dominated loading mode. Focusing the effects of different paths on the sand-pile interface shear behaviours, a series of cyclic interface shear tests have been conducted, in which two types of sands and four typical shear paths were adopted. It has been revealed that during continuous jacking process, the sample volume response changes significantly with different interface shear paths. The previous shear path also plays a key role in the cyclic degradation of interface strength with CNS (constant normal stiffness) condition. If the sample contraction is small during jacking process, the cyclic degradation of interface strength is obvious. But, when the sample contraction during jacking process is significant, the interface strength degradation is largely suppressed. This is mainly because the abundant broken fine particles along the pile shaft will fill into the voids and make the sand sample near the interface much denser. It is shown that the changes of pile-soil interface characteristics will affect the pile responses.