In the present study, glucose-responsive polymeric complex micelles based on the complexation of phenylboronic-acid-based (PBA-based) block copolymer and diol-functionalized polymers are reported. The phenylboronicacid- and diol-based block copolymers were successfully synthesized in only two reaction steps using reversible addition-fragmentation chain-transfer (RAFT) polymerization and postpolymerization modification of the obtained poly[(Nacryloylmorpholine-block-(N-acryloylmorpholine-co-pentafluorophenyl acrylate)], poly[(AMP-b-(AMP-co-PFPA)1, reactive block copolymer. The self-assembly of the complex micelles was investigated under neutral conditions using dynamic light scattering (DLS) and transmission electron microscopy (TEM). The interaction of the PBA block copolymer and diolcontaining polymer via boronate ester bond was investigated by H-1 NMR and UV-vis spectroscopy. The complex micelles enhanced the glucose responsiveness under physiological conditions compared to simple PBA micelles. Furthermore, the successful glucose-triggered release of FITC-insulin from the polymeric micelles was investigated.