A cleaning head for an in-floor pool cleaning system is provided. The cleaning head includes a sleeve having a passage and an insert extending through the passage of the sleeve. The insert includes a flow path and an aperture, wherein the flow path is a curved, such as a question mark shape, and exits through the aperture. The insert is moveable between a first position with the aperture retained with in the sleeve and a second position with the aperture extending beyond the sleeve. The flow path may include an overturn at the aperture. The insert includes a nozzle, a nozzle housing, an upper guide, a lower guide and a weight with the flow path extending through each component. The nozzle includes an angled inlet opening that corresponds to an angled outlet opening of the nozzle housing that engage each other when the nozzle is coupled within the nozzle housing.