Planted woodland islets act as sources of seed that may accelerate woodland development in extensive agricultural landscapes. We assessed a 1-ha plot that was planted with 16 100-m2 islets of holm oak Quercus ilex subsp. ballota seedlings near Toledo (Spain) in 1993. In spring 2014 we measured (1) acorn predation and (2) seedling emergence from seeded acorns at different distances from and orientations around the islets with half of the acorns protected to prevent predation, (3) survival of emerged seedlings, and (4) natural tree establishment outside of the planted islets. Most (96.9 %) unprotected acorns were removed or predated. Seedling emergence from protected acorns ranged from 42.9 % on the northern side of the islets to 13.2 % on the southern side, suggesting a less stressful microclimate on the northern side. Survival of naturally established seedlings was 28.6 % by the end of first summer; seedling mortality was chiefly due to drought (45.0 %) and herbivory (35.0 %). Density of emerged seedlings, surviving seedlings after first dry season, and established oaks >1-year old was similar at different distances from the islets. Over the 21 year time period, 58 new oak individuals >1-year old have established (an average of 3.3 established individuals per ha per year) at an average distance of 6.3 ± 5.4 m away from the closest islet. We conclude that initial oak regeneration triggered by small planted islets in Mediterranean abandoned farmland is slowed down by high acorn predation, seedling herbivory, and stressful microclimatic conditions. Regardless, these islets are a viable tool for regeneration of Mediterranean oak woodland.