In this study, the duration-of-load effect on the rolling shear strength of cross laminated timber (CLT), with different cross-sectional layups (five-layer and three-layer), was evaluated. A stress-based damage accumulation model is chosen to evaluate the duration-of-load strength adjustment factor of 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 has been calibrated and verified based on the test data from low cycle trapezoidal fatigue tests (damage accumulation tests) in the previous study. 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 based reliability assessment of the CLT products, considering short-term, snow, and dead load only loading cases. The reliability analysis results and factors reflecting the duration-of-load effect on the rolling shear strength of CLT are compared and discussed. The characteristic of this modeling theory lies in that the verified model is also able to predict the duration-of-load behaviour of CLT products under arbitrary loading history, such as long-term dead load case; then, these predictions of time to failure from the damage accumulation model can elucidate duration of load by the stress ratio evaluation approach. The results suggest that the duration-of-load rolling shear strength adjustment factor for CLT is more severe than the general duration-of-load adjustment factor for lumber; this difference should be considered in the introduction of CLT into the building codes for engineered wood design.