Water-repellent (hydrophobic) soils do not wet instantaneously, but only after some time (a few seconds to hours) of soil-particle contact with water. Some plant species can render soils hydrophobic but in this respect, olive trees have scarcely been examined. Measurements of water repellency in olive orchards of different ages in different locations in Israel using the water drop penetration time (WDPT) test have shown that soils tend to become hydrophobic, regardless of texture and structure. A comprehensive study was then performed for an irrigated young and mature olive grove and nearby uncultivated bare soil in the southern part of Israel. The study included intensive WDPT measurements, initial (repellency intensity) and rate of decrease (repellency persistence) for sessile drops placed on the soil surface, cumulative infiltration using tension disc infiltrometer, and monitoring flow in a transparent flow chamber packed with soils from the different plots. The soil from the mature olive plot was noticeably more water repellent than the young plot's soil, and both differed from the uncultivated soil that was fully wettable. The contact angle of a drop placed on the surface of a single layer of soil particles decreased exponentially with time, with a lower decay rate for the mature orchard soil. Cumulative infiltration had a convex pattern for wettable soils and a concave pattern for water-repellent ones. The difference in infiltration pattern was attributed to water/pressure buildup behind the wetting front as a result of the dynamic contact-angle-induced pore resistivity to wetting. The supplemental pressure, also known as dynamic water-entry pressure, increases the infiltration rate beyond that obtained by the capillary pressure per se. The significant correlation between soil sorptivity and the asymptotic infiltration rate, both calculated from the cumulative infiltration curves, and the WDPT substantiates the dependence of pressure overshoot and the rate at which the contact angle decreases prior to pore wetting. The considerable differences in plume shape, size, and internal saturation distribution between the wettable and water-repellent soils, indicating unstable flow in the latter, were also explained by the wettability-dependent water-entry pressure. The outcome of this study indirectly supports the findings that higher surface runoff and erosion are associated with no-till farming in olive orchards, due to the combination of no-till cropping and the near-surface accumulation of hydrophobic organic carbon compounds.