Herein, we reported a novel surface based chemosensor, a highly chiral responsive surface recognized galactose enantiomer based on the self-assembly system, which exhibits highly efficient chiral selective for D-galactose via contact angle measurements (CA). We primarily studied the interaction between S-phenethylamine-calix[4]arene (S-DPC4A) and L/D-galactose through the characterization of ¹H NMR spectroscopic and UV spectroscopic, then a functional S-DPC4A-based sensing surface were constructed by click reaction and characterized by the analysis of contact angle and X-ray photoelectron spectroscopy (XPS). Interestingly, the S-DPC4A-based sensing surface exhibited highly dynamic responsive for the D-galactose on the tilted interface, realized the weak chiral-interaction signals to convert into the macroscopic properties of materials and reached visual distinction accompanying the changes of surface wettability.