Understanding and predicting the behaviour of wind turbine wake flows over hills is important for optimal design of wind-farm configurations on topography. In this study, we present an analytical modelling framework together with large-eddy simulation (LES) results to investigate turbine wakes over two-dimensional hills. The analytical model consists of two steps. In the first step, we deal with the effect of the pressure gradient on the wake evolution; and in the second step, we consider the effect of the hill-induced streamline distortion on the wake. This model enables us to obtain the wake recovery rate, the mean velocity and velocity deficit profiles and the wake trajectory in the presence of the hill. Moreover, we perform LES to test our model and also to obtain new complementary insight about such flows. Especially, we take advantage of the LES data to perform a special analysis of the behaviour of the wake on the leeward side of the hill. It is found that the mainly favourable pressure gradient on the windward side of the hill accelerates the wake recovery and the adverse pressure gradient on the leeward side decelerates it. The wake trajectory for a hill of the same height as the turbine’s hub height is found to closely follow the hill profile on the windward side, but it maintains an almost constant elevation (a horizontal line) downstream of the hilltop. The trajectory of the wake on the leeward side is also studied for a limiting case of an escarpment, and it is shown that an internal boundary layer forms on the plateau which leads to an upward displacement of the wake centre. Finally, a parametric study of the position of the turbine with respect to the hill is performed to further elucidate the effect of the hill-induced pressure gradient on the wind turbine wake recovery.