Phenylboronic acid-containing thermo-responsive block copolymer, poly(ethylene oxide)-b-poly (methoxydi(ethylene glycol) methacrylate-co-aminophenylboronic acid ethyl methacrylate) (PEO-b-P (DEGMMA-co-PBAMA)), was employed to investigate the multiple micellization and dissociation transitions. The unique sugar-and pH-responsive properties of phenylboronic acid were interesting to provide two parallel approaches to tune the critical micellization temperature (CMT) and multiple micellization of thermo-responsive block copolymer. The block copolymers were molecularly soluble below 21 C and underwent micellization above 21 C at pH 8.7. After glucose was added at 24 C, hydrophobic phenylboronic acid was changed to hydrophilic boronateeglucose complex and the CMT of the thermo-sensitive block was increased which caused the dissociation of micelles. In parallel, if the solution pH was increased from 8.7 to 11 at 25 C, micelles were disrupted because of the formation of hydrophilic phenylboronate anion, which elevated the CMT of the thermo-sensitive block polymer. The introduction of phenylboronic acid groups into the thermo-responsive block copolymers provides a novel approach to tune the multiple micellization and dissociation transitions that might have great potentials in biomedical applications.