An experimental and numerical study was conducted to investigate the effects of dimple shapes on the heat transfer and flow friction of a turbulent flow over dimpled surfaces with different dimple shapes: spherical, teardrop, elliptical, and inclined elliptical. These dimples all have the same depth. The heat transfer, friction factor, and flow structure characteristics in the cooling channels with dimples of different shapes have been obtained and compared with each other for a Reynolds number range of 8500–60,000. The study showed that the dimple shape can have distinctive effects on the heat transfer and flow structure in the dimpled channels. The teardrop dimples show the highest heat transfer, which is about 18% higher than the conventional spherical dimples; and the elliptical dimples have the lowest heat transfer, which is about 10% lower than the spherical dimples; and however the inclined elliptical dimples have comparable heat transfer and pressure loss performance with the spherical dimples. The experiments still showed the realistic heat transfer enhancement capabilities of the dimpled channels relative to a smooth rectangular channel flow under the same flow and thermal boundary conditions, even after considering the thermal entrance effects in the channel flow and the enlarged heat transfer (wetted) area due to the dimpled surface. The three-dimensional numerical computations showed different vortex flow structures and detailed heat transfer characteristics of the dimples with different shapes, which revealed the influential mechanisms of differently shaped dimples on the convective heat transfer enhancement.