This paper presents a method to analyze probabilistic anisotropic initial damage of a rock mass. A three-dimensional geometric model of cracks in a rock mass is established in terms of several parameters, such as orientations, spacing and normalized sizes of cracks in the rock mass. The dip, dip direction, spacing, and normalized size of cracks of the Bukit Timah granite in Singapore were obtained from visual inspection of rock cores, color TV imaging, and impression packer tests in the boreholes at a site of geological investigation. Using the measured data, probabilistic distribution laws of geometric parameters of cracks on the surface of the boreholes are derived. Based on these statistical distributions and using Monte-Carlo simulation method, the distribution of anisotropic initial damage of the Bukit Timah granite is derived and found to have a beta distribution. This anisotropic initial damage distribution of a rock mass can be used in probabilistic analysis of rock mass responses to both static and dynamic loads.