Diabetic patients are more susceptible to chronic hand infection. Due to mixed bacterial infection, poor wound healing capacity, associated neuropathy and angiopathy, they suffer mostly from deep hand infection, which necessitates multiple surgeries and reconstruction of the defect. Early partial amputation of the digit followed by coverage of the soft tissue defect by flap and timely physiotherapy can provide satisfactory functional outcome in chronic severe hand infection cases. We report and compare two similar cases of chronic severe diabetic hand infection where differences in timing of partial amputation, coverage of the defect by groin flap and adequate postoperative rehabilitation made a gross difference in the final functional outcome.