Diabetes is an important modifying factor of periodontitis, but its association with peri-implant diseases has not been fully explored and the existing literature reports controversial results. The aim of this retrospective study was to evaluate the influence of diabetes on peri-implantitis and implant failure. Smoking status, history of periodontal disease, presence of diabetes, diabetes type, therapy and glycaemia levels were collected in a total of 204 subjects treated with 929 implants, with a mean follow-up time of 5.7 ± 3.82 years after loading. Odds ratio (OR) for diabetes as a direct cause of peri-implantitis and implant failure were calculated, adjusted for smoking status and history of periodontitis. Nineteen patients were diabetic and most of them presented a good control of the disease at the time of surgery. The overall patient-level prevalence of peri-implantitis was 11.3%. Among diabetic patients, one developed peri-implantitis, whereas one experienced multiple implant failures. The calculated ORs, adjusted for smoking status and periodontitis, were not statistically significant. The results revealed no association between diabetes and peri-implantitis or implant failure coherently with the existing scientific literature. The actual influence of hyperglycemia on implant failure is still uncertain and new studies with larger cohorts of patients are needed.