The roof sheathing panels on low-rise buildings have suffered serious damage under strong winds. Fast and accurate damage assessments for roof sheathing panels are desired for damage mitigation and risk management. However, existing models rarely take into account wind directionality effect. Few models that consider this effect by some authors of this paper involve Monte Carlo simulation method, which is cumbersome and has less flexibility in terms of simulation efficiency. This study presents a probabilistic analysis framework for wind damage assessment with various mean recurrence intervals (MRIs) considering directionality. To achieve these estimations more efficiently, a novel moment-based estimation approach is developed, in which a set of formulas to determine damage ratio's first four moments and panels' failure probabilities are derived. For easy application in practice, a simplified approach for modeling directionality effect in estimation of damage ratio with a given MRI is further proposed. Performances of proposed approaches are evaluated by a comprehensive numerical example. Results showed the proposed moment-based approach can present satisfactory estimation accuracy. It is also confirmed the wind directionality effects on damage ratio estimations with a given MRI can be simply but well modeled using the proposed simplified approach.