This study presents experimental results on evaporation and drainage in both wettable and water-repellent sands whose surface wettability was artificially modified by silanization. The 2D optical and 3D X-ray computed tomographic imaging was performed during evaporation and the water retention during cyclic drainage and infiltration was measured to assess effects of wettability and initial wetting conditions. The evaporation gradually induces its front at the early stage advance regardless of the wettability and sand types, while its rate becomes higher in water-repellent Ottawa sand than the wettable one. Jumunjin sand which has a smaller particle size and irregular particle shape than Ottawa sand exhibits a similar evaporation rate independent of wettability. Water-repellent sand can facilitate the evaporation when both wettable and water-repellent sands are naturally in contact with each other. The 3D X-ray imaging reveals that the hydraulically connected water films in wettable sands facilitate the propagation of the evaporation front into the soil such that the drying front deeply advances into the soil. For cyclic drainage-infiltration testing, the evolution of water retention is similar in both wettable and water-repellent sands when both are initially wet. However, when conditions are initially dry, water-repellent sands exhibit low residual saturation values. The experimental observations made from this study propose that the surface wettability may not be a sole factor while the degree of water-repellency, type of sands, and initial wetting condition are predominant when assessing evaporation and drainage behaviors.