This paper presents a study on rolling shear damage accumulation and duration of load of cross-laminated timber (CLT) with low cycle fatigue tests. The study of the duration-of-load (DOL) effect on strength properties of wood products is typically challenging; it may be more challenging for non-edge-glued CLT considering crosswise layups of wood boards, existing gaps, and non-uniform stress distributions in cross layers. In experimental studies, short-term ramp loading tests and low cycle trapezoidal fatigue loading tests were used to study the DOL behaviour of the CLT rolling shear. The ramp tests were performed to establish the short-term CLT rolling shear strength properties. The low cycle trapezoidal fatigue tests were performed to evaluate the damage accumulation process for the matched specimens under controlled rolling shear stress levels. A stress-based damage accumulation model was further used to investigate the rolling shear DOL effect with model parameters treated as random variables calibrated against one set of the test data. The calibrated model predicted well comparing with the other set of the test data. This verified model provides a robust tool to quantify the DOL effect on rolling shear strength in the core layers of CLT that can be used in future studies of DOL behaviour in CLT under arbitrary loading histories.