Tornadoes and hurricanes create high suction pressures on roofs, making the roof sheathing-to-rafter connection a critical part of the structural load path in light-frame wood (LFW). Past studies have characterized the uplift capacity of fastened roof sheathing connections; however, the connection’s cyclic characterization has garnered little research attention and is necessary for robust finite element analysis of LFW structures. Long-duration hurricane winds can induce cyclic loads on roof sheathing, which may weaken fastened connections over time and increase the risk of progressive damage. The present study addresses this gap by investigating the cyclic behavior of twelve variations of LFW sheathing-to-rafter connections, including variations of sheathing type and fastener type and count. Monotonic and cyclic test results are compared and evaluated against empirical capacity estimates calculated using specified design equations. Key cyclic parameters, such as ductility, initial stiffness, energy dissipation, strength degradation, and equivalent viscous damping, are analyzed to capture both the elastic response and progressive deterioration under repeated loading. The results show that the peak capacity under cyclic loading was reduced by approximately 14 – 33% from monotonic loading for nailed connections, with statistically significant reductions observed for the plywood-nail P-N-1F and P-EN-2F configurations. A parametric sensitivity analysis showed that fastener type was the dominant variable affecting cyclic peak capacity, while sheathing type was not statistically significant. Furthermore, nailed connections, particularly with oriented strand board sheathing, exhibit reduced capacities compared to empirical estimates, with measured-to-calculated ratios as low as 68%. These results suggest that current design standards, which primarily rely on monotonic testing, may overestimate actual performance under high-wind conditions. These findings can inform updates to building codes and design standards, guide construction best practices, and enhance the structural resilience of LFW structures in high-wind regions.