In our study, we investigated whether root hydraulic conductance is related to post-transplant recovery. We used two Quercus species that differ in their transplant ability, Q. bicolor and Q. macrocarpa. Q. bicolor easily survives transplanting, whereas Q. macrocarpa often does not. We compared root hydraulic conductance after transplanting between control (without root pruning) and root-pruned, 1-year-old, small-caliper trees. We also examined the effects of transplant timing on post-transplant recovery of large-caliper trees. Hydraulic conductance in fine roots was correlated with recovery of the two Quercus species after transplanting. Six months after transplanting, small-caliper Q. bicolor trees had similar specific hydraulic conductance (KS) in fine roots compared with the KS before root-pruning, whereas fine root KS in small-caliper Q. macrocarpa trees decreased. Lower pre-dawn and midday xylem water potential in root-pruned Q. macrocarpa 6 weeks after transplanting indicates that root-pruned Q. macrocarpa experienced transplanting-induced water stress. For large-caliper trees, all Q. macrocarpa trees exhibited typical symptoms of transplant shock regardless of transplant timing, which was the result of higher vulnerability to mild water stress compared with Q. bicolor, resulting in a large reduction in fine root KS. Fine root KS in spring-transplanted Q. bicolor trees was much higher than that in fall-transplanted trees, implying spring transplanting is optimal for Q. bicolor. Other intrinsic characteristics of the species should be considered in the future when making better decisions on transplant timing such as xylem anatomy, carbon storage, rhizosphere conditions, and plant growth.