Windbreaks and shade nets are used in South Africa to protect fruit orchards from wind scar damage, thereby avoiding major export quality losses. In the Western Cape, strong southeasterly winds (>3.6–4.5 m s–1) during spring and summer are the main causes of significant external peel damage. In this study, wind scar damage on ‘Tango’ and ‘Nadorcott’ mandarins, as well as ‘Ruby Star’ plums, was quantified at various distances from tree-based windbreaks around Stellenbosch, Western Cape, South Africa. The wind speed was consistently higher at 16H compared to 3H after flowering (November–February). The highest pack out (class 1 fruit) was observed near the windbreak (3H) and decreased as the distance increased towards 10H and 16H. There were no significant differences in the incidence of severe wind scar damage between the distance treatments. Most of severe wind scar damage (86%) occurred within the first 12 weeks after petal drop, during the highest wind incidence. Maximum wind speed reductions were observed between 2H and 4H from the established windbreaks. Our results confirmed the impact of wind on external fruit quality and highlighted the limitation of tree-based windbreaks as distance increases, which partly supports the current trend towards full enclosure of orchards with shade nets.