Insect pre-dispersal seed predators attack a large proportion of the acorn crops in oak forests worldwide. Oaks (Quercus spp.) have evolved several strategies, including physical barriers, chemical defenses (e.g., tannins), and/or phenological predator avoidance, to reduce infestation rates. This study examines how four Mediterranean oak species cope with acorn-feeding insects. Nearly 4000 acorns were collected from five sites at two time points during the maturation period: in mid-September and mid-October. Infestation rates were higher in mid-September, when the pericarp is softer and easier to drill, but at that time, the cotyledon tannin content was higher. Q. coccifera acorns had the highest tannin concentration, which, we experimentally discovered, hampered weevil development (with longer development and a lower final larval mass). Infested acorn abscission was also more effective in Q. coccifera. Due to the smaller size and later maturation phenology of its acorns, insects depleted the cotyledons and suffered food shortages more frequently. In the end, Q. coccifera showed the lowest acorn infestation rates, although its strategy would have costs in further stages of the regeneration cycle. Tannins deter acorn dispersers, and their production is costly. Such trade-offs would favor the co-existence of different strategies evolved by Quercus spp. against pre-dispersal insect predators.