In this study, the duration-of-load (DOL) effect on the rolling shear strength of cross laminated timber (CLT) was evaluated. A stress-based damage accumulation model is chosen to evaluate the DOL effect on the rolling shear strength of CLT. This model incorporates the established short-term rolling shear strength of material and predicts the time to failure under arbitrary loading history. The model was calibrated and verified based on the test data from low cycle trapezoidal fatigue tests (the damage accumulation tests). The long-term rolling shear behaviour of CLT can then be evaluated from this verified model. As the developed damage accumulation model is a probabilistic model, it can be incorporated into a time-reliability study. Therefore, a reliability assessment of the CLT products was performed considering short-term and snow loading cases. The reliability analysis results and factors reflecting the DOL effect on the rolling shear strength of CLT are compared and discussed. The results suggest that the DOL rolling shear strength adjustment factor for CLT is more severe than the general DOL adjustment factor for lumber; and, this difference should be considered in the introduction of CLT into the building codes for engineered wood design.