One option for coping with the high soil salinity levels caused by saline, shallow groundwater conditions along the west side of the San Joaquin Valley is to convert from sprinkler or surface irrigation methods to drip irrigation. Experiments in commercial fields revealed that subsurface drip irrigation of processing tomato (Lycopersicon esculentum Mill. var. esculentum) is highly profitable under these conditions compared with other irrigation methods. The experiments also showed that little or no field-wide leaching occurred, based on the conventional or water balance approach to estimating the leaching fraction (LF), yet soil salinity measurements showed considerable leaching around the drip lines. Actual LFs could not be calculated because LF, soil salinity, soil water content, and root density all varied with distance and depth around the drip lines. Therefore, we conducted a numerical modeling study using the HYDRUS-2D computer simulation model to evaluate leaching with drip irrigation under saline, shallow groundwater conditions for different amounts of applied water, water table depths, and irrigation water salinity, described by the electrical conductivity of the irrigation water (ECiw). Results showed that LF values ranged from 7.7 to 30.9% as applied water amounts increased from 60 to 115% of the potential evapotranspiration (ETpot) for the ECiw = 0.3 dS m−1 irrigation water, even though the water balance method showed no leaching for applied water amounts equal to or smaller than ETpot. The spatially varying soil wetting patterns that occur under drip irrigation caused the localized leaching, which was concentrated near the drip line.