Regulation of agricultural pests managing their natural enemies represents an alternative to chemical pesticides. We assessed the potential of insectivorous birds as pest regulators in woody crops located in central Spain. A total of 417 nest boxes installed in five field study sites (one vineyard, two fruit orchards, and two olive groves) were monitored for use and breeding of insectivorous birds and other species for four consecutive years (2013-2016). At all field sites except the two olive groves, where birds never occupied the nest boxes, predation experiments were conducted with Greater wax moth (Galleria mellonella) sentinel caterpillars, and food consumption by birds was estimated. Nesting of insectivorous birds, chiefly Great tit (Parus major), and sparrows (Passer domesticus and P. montanus) increased over time, averaging 60% per field site in the vineyard and fruit orchards by the fourth year. Use of nest boxes by sparrows and by Garden dormouse (Eliomys quercinus) was high at the fruit orchards (70%) and the vineyard (30%), respectively. Micro-habitat characteristics (nest box level) and meso-habitat characteristics (patch level) strongly affected use of nest boxes and bird breeding (i.e. number of laid eggs and produced chicks) in different years. Distance to natural or semi-natural vegetation did not consistently affect bird breeding, nor did we see consistent evidence of competition between adjacent breeding birds. Predation rates of sentinel caterpillars were approximately one-third higher near boxes with nesting birds (31.51 ± 43.13%) than at paired distant areas without nest boxes (22.45% ± 38.58%). Food consumption by insectivorous birds per ha and breeding season were conservatively estimated to range from 0.02 kg in one fruit orchard to 0.15 kg in the vineyard. We conclude that installation of nest boxes in Mediterranean woody crops enhances populations of insectivorous birds that regulate pests, but that the effects are moderate and highly context-dependent.