Numerical investigation of the compressible flow past an 18% thick circular-arc aerofoil was carried out using detached-eddy simulation for a free-stream Mach number M∞ = 0.76 and a Reynolds number Re = 1.1 × 107. Results have been validated carefully against experimental data. Various fundamental mechanisms dictating the intricate flow phenomena, including moving shock wave behaviours, turbulent boundary layer characteristics, kinematics of coherent structures and dynamical processes in flow evolution, have been studied systematically. A feedback model is developed to predict the self-sustained shock wave motions repeated alternately along the upper and lower surfaces of the aerofoil, which is a key issue associated with the complex flow phenomena. Based on the moving shock wave characteristics, three typical flow regimes are classified as attached boundary layer, moving shock wave/turbulent boundary layer interaction and intermittent boundary layer separation. The turbulent statistical quantities have been analysed in detail, and different behaviours are found in the three flow regimes. Some quantities, e.g. pressure-dilatation correlation and dilatational dissipation, have exhibited that the compressibility effect is enhanced because of the shock wave/boundary layer interaction. Further, the kinematics of coherent vortical structures and the dynamical processes in flow evolution are analysed. The speed of downstream-propagating pressure waves in the separated boundary layer is consistent with the convection speed of the coherent vortical structures. The multi-layer structures of the separated shear layer and the moving shock wave are reasonably captured using the instantaneous Lamb vector divergence and curl, and the underlying dynamical processes are clarified. In addition, the proper orthogonal decomposition analysis of the fluctuating pressure field illustrates that the dominated modes are associated with the moving shock waves and the separated shear layers in the trailing-edge region. The results obtained in this study provide physical insight into the understanding of the mechanisms relevant to this complex flow.