A series of numerical experiments have been carried out on the water entry problem of three-dimensional multi-degree-freedom cylinders. The circular cylinder was released above the water with a specified inclined angle and velocity at entry. The hydrodynamics of the water entry problem have been investigated numerically. The Piecewise Linear Interface Calculation (PLIC) schemes have been applied in conjunction with the Volume of Fluid (VOF) method to capture the interface. Overset meshes have been adopted to handle the moving object. The numerical model is built on the framework of OpenFOAM which is an open-source C++ toolbox. Numerical results have been obtained. Transient flow and pressure distributions have been generated. The presence of air entrapment which has been reported experimentally has also been confirmed in the numerical solution. The fluid physics of the oblique water entry problem such as the formation and development of the air entrapment has been explored. The transient positions and inclined angles of the moving circular cylinder have been found to be in good agreement with the experimental results. Parametric studies have been performed with major findings reported.