This chapter deals with a various kind of boronic acid-based supramolecular systems. When a boronic acid moiety is introduced into a gelator, the supramolecular self-assembling process becomes controllable by addition of sugars. This molecular design results in the sugar-responsive sol-gel transformation. By combining porphyrin and boronic acid, supramolecular systems that exhibit guest-induced spectroscopic changes are created. The air-water interface is utilized for constructing two-dimensionally ordered self-assembly of boronic acid-appended amphiphiles. This system exhibits unique molecular recognition behaviors that are not observed in homogeneous solution systems. Boronic acid-functionalized metal nanoparticles are demonstrated to act as useful platforms for spectroscopic sugar sensing. The aggregation behavior of nanoparticles is regulated by sugars, resulting in changes in fluorescence emission, surface plasmon resonance, etc. Boronic acid-appended polymers also appear as a unique class of stimuli-responsive polymers with many potential applications. In this chapter, the three different types are covered: (i) polymers containing boronic acid in the main-chain, (ii) boronic acid-appended polymers, and (iii) self-assembly of boronic acids onto polymers. In the final section, the usefulness of boronic acid-based thin films for colorimetric saccharide sensing is described.