Water within pavement layers is the major cause of pavement deteriorations. High water content results in significant reduction in soil’s resilient behavior and increase in permanent deformation. Conventional drainage systems can only drain gravity water but not capillary water. Both preliminary lab and field tests have proven the drainage efficiency of a newly developed H2Ri geotextile with wicking fabrics. This bio-wicking system aims at resolving the potential issues that the original design may encounter: (1) H2Ri ultraviolet degradation, (2) H2Ri mechanical failure, (3) loss of drainage function under high suction, and (4) clogging and salt concentration. Both elemental level and full-scale test results indicated that the bio-wicking system is more effective in draining capillary water within the base courses compared with original design, in which the geotextile is directly exposed to the open air. However, a good drainage condition is required for the bio-wicking system to maintain its drainage efficiency. Accumulation of excess water will result in water re-entering the road embankment. Moreover, grass root and geotextile share the same working mechanism in transporting water. In the proposed bio-wicking system, the relatively smaller channels in the grass roots further ensures water moving from H2Ri geotextile, transporting through the stems of grass, and eventually evapo-transpiring into the air at the leaf-air interfaces. In sum, the bio-wicking system seemed to successfully address the concerns in the preliminary design and is a more efficient system to dehydrate the road embankment under unsaturated conditions.