Connections are responsible for maintaining the integrity and safety of wood structures when subjected to lateral force induced by wind or seismic event. The aim of this study is to provide a better understanding of monotonic and cyclic response of timber-to-timber nailed connections. A total of 48 groups of double-shear nailed connections were tested to investigate the effect of different variables on the lateral resistance performance of connections. Representative parameters derived from practical nailed timber connections were considered, including nail diameter, nail type, and load-to-grain angle. It is found that the failure modes of the specimens loaded monotonically are attributed to bending yield of nails. Conversely, under cyclic loading, the majority of nail failures occur as a result of fatigue fracture, which is caused by the repetitive bending stress. A reduction in ductility ranging from 76.9 % to 92.7 % is observed in specimens subjected to cyclic loading, as compared to those under monotonic loading. Utilizing larger-diameter nails as connectors can markedly improve the load-bearing capacity, ductility, and energy-dissipation capabilities of connections subjected to cyclic loading. Helically threaded nails (HTN) have a 29.4 % higher lateral capacity than smooth shank nails (SSN), but a 29.9 % lower stiffness and 22.9 % lower ductility. Experimental load capacities were compared with existing calculation models, and Eurocode 5 was identified as the most suitable design code for predicting the lateral performance of nailed timber joints. Two analytical models were proposed to better simulate the load-slip behavior of nailed connections under monotonic and cyclic loading conditions, respectively.