This study reports the formation of a hydrogel generated by polymerizing aminophenyl boronic acid in polyvinyl alcohol (PVA). The gel formed as a result of complexation between the -OH groups of PVA, and boronic acid moieties were stable and exhibited high degree of swelling proportional to the concentration of glucose. Extended swelling was attributed to the strong affinity of the gel to glucose and to the subsequent breaking of the bond formed between PVA and boronic acid groups. Interestingly, the gel was found to bind a high amount of glucose. We evaluated the hydrogel in terms of its ability to bind glucose and to release ciprofloxacin. Retention of antibacterial efficacy of the released drug was also demonstrated. Features such as swelling, drug release, and glucose binding reflect the possibility of tuning a new dressing for wounds particularly in diabetic patients.