The present study aims to investigate the synchronization characteristics of a pitch–plunge aeroelastic system subjected to coupled structural free-play and dynamic stall-induced aerodynamic nonlinearities. The semi-empirical Leishman–Beddoes (LB) aerodynamic model is used to capture the dynamic stall phenomena at large angles-of-attack (AoA). A bifurcation analysis, considering the flow-speed as the control parameter, reveals that the free-play nonlinearity is primarily responsible for the dynamical transition in the presence of the attached flow. In this case, a pitch and plunge frequency coalescence takes place through an aperiodic to periodic signature transition. Furthermore, by tracking the flow specific variables estimated using the LB model, it is observed that the onset of the dynamic stall plays a pivotal role in the bifurcation scenario at high flow speed regimes, marking the presence of stall flutter. The framework of synchronization is used to discern the response dynamics at low speed and high speed flow regime by estimating the pitch and plunge modal frequencies and their corresponding phase components. The routes to synchronization are identified to be through phase-locking (frequency coalescence) and through suppression of the plunge mode by the dominance of pitching frequency in the regimes before and after the onset of dynamic stall, respectively. Finally, it is shown that the different synchronization routes can possibly be a useful tool to identify the presence of stall flutter oscillations in a coupled aeroelastic system. © 2021