Diabetes mellitus (DM) is a common comorbidity and risk factor for postoperative complications in head and neck (H&N) microsurgical reconstructions. Our study focused on the association between DM and individual complications regarding both surgical and medical aspects. A meta-analysis of English-language articles comparing a series of complications between DM and non-DM H&N free-flap recipients was performed by comprehensive meta-analysis (CMA). Twenty-seven articles presented 14,233 H&N free-flap reconstructions, and a subset of 2329 analyses including diabetic cases was included for final analysis. Total postoperative (RR = 1.194, p < 0.001; OR = 1.506, p = 0.030) and surgical (RR = 1.550, p = 0.001; OR = 3.362, p < 0.001) complications were increased in DM subjects. Free-flap failure/necrosis (RR = 1.577, p = 0.001; OR = 1.999, p = 0.001) and surgical site infections (OR = 2.414, p < 0.001) were also increased in diabetic recipients. However, return to the operating room, dehiscence, fistulas, plate exposures, readmissions, and mortalities were not increased in DM patients. DM increased various complications in H&N free-flap reconstructions. Surgical indications should be cautiously evaluated, and aggressive treatments should be implemented for high-risk recipients.