The objective of this paper is to investigate two types of cloud shedding processes around the NACA66 (mod) hydrofoil with emphasis on the formation of the re-entrant flows and the transformation of varying shedding modes. The LES method combines the Schnerr-Sauer cavitation model in OpenFOAM to capture the detailed flow structures. Combining the experimental observation, the cloud shedding process can be divided into main re-entrant flow mode, transition mode, and side re-entrant flow mode. The re-entrant flow is primed from the middle of the attached cavity closure for the main re-entrant flow pattern. The velocity is more stable as it develops in a fan shape towards the leading edge of the hydrofoil. For the side re-entrant flow mode, the rotation and local collapse of cloud cavity in the previous cycle resulted in the incipient of the side re-entrant flow. Compared with the main re-entrant flow, the velocity of the side re-entrant flow fluctuates more significantly. The transition between the side re-entrant flow mode and the main re-entrant flow mode can be characterized by the normalized cavity length (lmax/c) and the cavity shedding frequency (St number).