Expanding tree canopies can be difficult to achieve in built environments because urban land is costly and urban soil inhospitable to vegetation so engineered planting systems offer a potentially valuable tool for achieving sustainable urban forests. Tree water uptake, performance and root distribution were assessed in systems of structural soil and structural cell. Structural soil relies on stone and soil, it is highly porous and designed to support tree root growth and possess pavement strength. The structural cell is made up of rigid structural units with 90% void space which is to be filled with soil. To evaluate tree performance under the conditions of fill and drain regimes in structural soil and structural cell, these two systems were subjected to three simulated infiltration rates. This study was conducted in April 2015 to April 2016 in the tropical equatorial environment of South East Asia. Infiltration rate affected both biomass accumulation and rooting depth. Species and substrate effect was significant for biomass and rooting characteristics but less prominent for transpiration. Biomass was greater for trees in structural cells, and Pouteria obovata was particularly sensitive to prolonged inundation. Rooting depth was always higher in the rapid infiltration indicating the negative effects inundation had on this parameter. Root system in the structural cell was deeper while those in the structural soil were wider. Samanea saman had better adapted to the drain and fill regimes, and this was despite Pouteria obovata being a coastal species and was expected to be flood tolerant. Species and substrate effect was weak (R2 ranging from 0.20 to 0.28) but moderate drainage consistently led to higher transpiration. We conclude that structural soil and structural cell are potential solutions and provide a tool to overcome suboptimal urban growing conditions. The application of these solutions will allow for seamless integration of greenery with urban infrastructure.