Stabilizing the hydrophobic wetting state on a surface is essential in heat transfer and microfluidics. However, most hydrophobic surfaces of Si are primarily achieved through microtexturing with subsequent coating or modification of low surface energy materials. The coatings make the hydrophobic surface unstable and impractical in many industrial applications. In this work, the Si chips’ wettability transitions are yielded from the original hydrophilic state to a stable transitional hydrophobic state by texturing bamboo-leaf-like hierarchical structures (BLHSs) through a diamond grinding wheel with one-step forming. Experiments showed that the contact angles (CAs) on the BLHS surfaces increased to 97° and only reduced by 2% after droplet impacts. This is unmatched by the current texturing surface without modification. Moreover, the droplets can be split up and transferred by the BLHS surfaces with their 100% mass. When the BLHS surfaces are modified by the low surface energy materials’ coating, the hydrophobic BLHS surfaces are upgraded to be superhydrophobic (CA > 135°). More interestingly, the droplet can be completely self-sucked into a hollow micro-tube within 0.1 s without applying external forces. A new wetting model for BLHS surfaces based on the fractal theory is determined by comparing simulated values with the measured static contact angle of the droplets. The successful preparation of the bamboo-leaf-like Si confirmed that transitional wettability surfaces could be achieved by the micromachining of grinding on the hard and brittle materials. Additionally, this may expand the application potential of the key semiconductor material of Si.