Planted woodland islets can provide seeds for restoring forest ecosystems in Mediterranean old fields lacking seed sources, but other factors than seed arrival can also hinder the establishment of woody species. We experimentally examined factors affecting the emergence, survival, growth and recruitment of holm oak (Quercus ilex) seedlings juveniles from 25-year-old 100-m2 oak woodland islets planted in a Mediterranean old field. Wet springs and summers increased seedling emergence and survival. Distance to the islets per se did not affect seedling performance. However, emergence and survival increased in microsites close to the islets in less sun-exposed orientations of the islets and far from the islets in more sun-exposed orientations. Damage by wild boar reduced emergence, and unsheltered seedlings had 26% lower survival than sheltered ones, reflecting herbivory. Herb community biomass and light reduction by herbs increased with distance from nearest islet; the sparse herb cover around islets was due to competition from woodland islets, not to herbivory. There was a mismatch between the pattern of seedling survival and how the abundance of naturally recruited oaks varied with distance from the nearest islet; this suggests that other drivers can counteract the spatial pattern of seedling survival. We conclude that natural regeneration of Q. ilex in old fields from planted woodland islets is slow (5.7 seedlings ha−1 yr−1) due to acorn and seedling predation, and drought during spring and summer. Despite their small size, planted islets affected survival of oak juveniles depending on the orientation and distance relative to the islets.