Genetic resistance is the most recommended measure to control verticillium wilt in olive (VWO), a vascular disease caused by the soil-borne fungus Verticillium dahliae, which has promoted the development of olive breeding programs aimed at obtaining new resistant and highly yielding cultivars in recent years. Screening has been commonly performed under controlled conditions in grow chamber after artificial inoculation during the early stage of breeding programs, but additional evaluation is necessary to confirm previous results as well as to test for additional agronomic traits. During this study, 20 breeding selections initially classified as resistant to the disease have been re-evaluated in artificially infested soils under natural environmental conditions. The maximum disease incidence (52.6%) was reached at 26 months after planting, and the disease intensity index reached the maximum value of 38.5% at 29 months after planting. Nine breeding selections consistently confirmed the previous results regarding resistance to V. dahliae infection; however, contradictory results, compared with those of previous evaluations under controlled conditions in grow chambers, were obtained for the rest of selections tested, thereby underlining the need for long-term experimentation under natural environmental conditions. Additional positive agronomic traits, such as early bearing, were also observed for some of the resistant selections, but plant vigor varied. Some seem highly promising for release as new cultivars when characterization of other important agronomic traits is completed in the future.