Cross-laminated timber (CLT) products are gaining popularity in the North American market and are being used in midrise wood buildings, in particular, in shearwall applications. Shearwalls provide resistance to lateral loads such as wind and earthquake loads, and therefore it is important to gain a better understanding of the behavior of CLT shearwall systems during earthquake events. This paper is focused on the seismic performance of connections between CLT shearwall panels and the foundation. CLT panels are very stiff and energy dissipation is accomplished by the connections. A literature review on previous research work related to damage prediction and assessment for wood frame structures was performed. Furthermore, a test program was conducted to investigate the performance of CLT connections subjected to simulated earthquake loads. Two different brackets in combination with five types of fasteners were tested under monotonic and cyclic loading protocols. In total, 98 connection tests were conducted and the monotonic load-displacement curves and hysteretic loops were obtained. In this paper, an energy-based cumulative damage assessment model was calibrated with the CLT connection test data. Finally, a correlation between the damage index and physical damage is provided.