Reducing forest stand density through silvicultural thinning has demonstrated potential to mitigate drought impacts on growth; however, less has been studied on how changes in stand structure created by different thinning methods influence forest growth responses to drought. This research examined the growth responses to drought of natural-origin red pine in a long-term study contrasting thinning methods. Dendrochronological methods were used to examine growth responses during several drought events among stands where different thinning methods have been applied since 1950. Growth responses to drought were expressed as resistance (maintaining growth during drought), and resilience (regaining pre-drought growth). Results indicate that periodic thinning from above, which resulted in smaller diameters, has the potential to moderate drought-induced growth reductions. Larger tree diameters negatively influenced tree-level resistance and resilience across all treatments; however, the proportion of dominant trees in a stand had contrasting effects on stand-level drought responses. Stands thinned from above exhibited more complex vertical structure and increased stand-level resistance and resilience to drought-induced growth declines because competition is more stratified among smaller diameter trees. Opposite trends were observed in stands thinned from below, where the larger diameters and monolayered structure create greater competition among trees of similar size and crown position. The results of this study highlight the utility in managing for greater structural diversity to mitigate the negative effects of drought in red pine forest ecosystems.