The unsteady flow physics and heat transfer characteristics due to interactions of periodic passing wakes with a separated boundary layer are studied using large-eddy simulation (LES). A series of airfoils of constant thickness with rounded leading edge are employed to obtain the separated boundary layer. Wake data extracted from precursor LES of flow past a cylinder are used to replicate a moving bar that generates wakes in front of a cascade (in this case, an infinite row of the model airfoils). This setup is a simplified representation of the rotor–stator interaction in turbomachinery. With a uniform inlet, the laminar boundary layer separates near the leading edge, undergoes transition due to amplification of disturbances, becomes turbulent, and finally reattaches forming a separation bubble. In the presence of oncoming wakes, the characteristics of the separated boundary layer have changed and the impinging wakes are found to be the mechanism affecting the reattachment. Phase-averaged results illustrate the periodic behavior of both flow and heat transfer. Large undulations in the phase-averaged skin friction and Nusselt number distributions can be attributed to the excitation of the boundary layer by convective wakes forming coherent vortices, which are being shed and convect downstream. Further, the transition of the separated boundary layer during the wake-induced path is governed by a mechanism that involves the convection of these vortices followed by increased fluctuations, where viscous effect is substantial.