Hay transfer is a promising method to restore temperate and subtropical grasslands, but its efficiency may depend on the harvesting timing and amount of hay used. We evaluated effects of harvest date (mid‐spring/November, early summer/December, and mid‐summer/February) and hay quantity (500 and 1000 g/m2) on vegetation cover, species richness, and species composition in an experimental study in subtropical southern Brazil for a period of 2 years. We transfer undried hay from a well‐conserved reference area onto a former grassland site degraded by pine plantations. Hay harvested during mid‐spring and early summer led to higher soil cover and species richness compared to the mid‐summer hay treatment in the first year of the experiment. A drought spell decreased vegetation cover in the second year following the hay transfer, with the mid‐spring hay treatment being the least affected. C3 grasses were more effectively introduced by mid‐spring and early summer hay, in contrast to C4 grasses that were better introduced by mid‐summer hay. Lower quantities of hay tended to lead to higher cover and species richness for all harvest dates. Freshly cut undried hay can be an effective way to reintroduce native species in degraded subtropical grasslands. We conclude that timing of hay collection and the amount of hay used influence vegetation cover and species composition at the restoration site and that multiple harvest dates increase restoration success. The drought in the second year of the experiment illustrates the need to consider the possibility of adverse climatic conditions in restoration planning.