The formation of dense understories in eastern forests has created low light environments that hinder the development of advance oak reproduction. Studies have shown that a midstory removal can enhance these light conditions and promote the development of competitive oak seedlings. Previous studies have been primarily focused on oaks found on productive sites, and there is little knowledge of this treatment’s potential on intermediate sites and the typically associated oak species. This study investigates the seven-year effects of midstory removal on natural and underplanted white (Quercus alba L.) and black oak (Quercus velutina L.) reproduction, as well as competing red maples (Acer rubrum L.), on intermediate sites within the western rim of the Cumberland Plateau. In addition to its effect on stand reproduction, this study also investigates the impact of this treatment on microclimate. Results from this study can provide a look at the long term success of midstory removal on intermediate quality sites and serve as a basis for future oak management in the region.