Pinning and depinning of a windswept droplet on a surface is familiar yet deceptively complex for it depends on the interaction of the contact line with the microscopic features of the solid substrate. This physical picture is further compounded when wind of the Reynolds number greater than 100 blows over pinned drops, leading to the boundary layer separation and wake generation. In this Rapid Communication, we incorporate the well-developed ideas of the classical boundary layer to study partially wetting droplets in a wake created by a leader object. Depending on its distance from the leader, the droplet is observed to exhibit drafting, upstream motion, and splitting, due to the wake-induced hydrodynamic coupling that is analogous to drafting of moving bodies. We successfully rationalize the onset of the upstream motion regime using a reduced model that computes the droplet shape governed by the pressure field inside the wake.