In underwater adhesion of a topographically patterned surface with a very soft material such as human skin, the elastic deformation can be large enough to achieve solid-on-solid contact not only on top of the hills but also in the valleys of the substrate topography. In this context, we have studied the dynamics of dewetting of a thin liquid film confined between a rigid, periodic micropillar array and a soft, elastic sphere. In our experiments, we observed two very distinct dewetting morphologies. For large ratios of array period to micropillar height and width, the dewetted areas tend to have a diamond-like shape and expand with a rate similar to a flat, unpatterned substrate. When the array period is reduced, the morphology of the dry spot becomes irregular and its expansion rate is significantly reduced. We developed a fully coupled numerical model of the dewetting process that reproduces the key features observed in experiments. Moreover, we performed contact mechanics simulations to characterize the deformation of the elastomer and the shape of the dewetted area in a unit cell of the micropillar array.