Inspired by the water-repellent and self-cleaning properties of the lotus leaf in the natural world, artificial superhydrophobic surfaces have attracted extensive interest in academia and industry. Static and dynamic hydrophobicities are very important phenomena in our daily life as well as in many industrial processes. However, the difference between these two phenomena has not been well understood. The objective of this study was to investigate and predict the sliding behavior of water droplets on silicone sheet surfaces with uniaxial groove structures. The groove structures were fabricated on silicone sheet surfaces by a molding process using three different molds with different groove widths. Increasing the groove width decreased the sliding angle. The sliding angle could be reduced to a greater extent than that of previously reported fluorinated hydrophobic surfaces, which exhibited sliding angles of less than 2°. The retention force between the water droplet and the silicone sheet surface was proportional to the contact ratio. It was found that the retention force was proportional to the shape of the water droplet on the surface at the sliding angle, especially the product of the contact angle hysteresis and the width of the contact line.