Diabetes and other medically compromising diseases may affect people in many ways. Missing teeth can be replaced by various methods including dental implants. The stability, a more natural appearance, and minimizing the risk of bone resorption attribute to its direct anchor into bones. Nevertheless, diabetic patients may experience failure of implant placement due to microvascular complications that lead to sluggish healing after surgery. In addition, some medications are believed to impair bone healing, thus compromising dental implant success. This paper evaluates osseointegration and crestal bone loss of implants placed in medically compromised patients. A retrospective cross-sectional study was conducted using patient records from Department of Prosthodontics, Saveetha Dental College, Chennai, from June 2019 to March 2020. Patients who had dental implants and were medically compromised were chosen randomly. Data were collected and then subjected to statistical analysis. Descriptive statistics analysis was done to find the correlation between crestal bone loss and medically compromised individuals. Microsoft Excel 2016 data spreadsheets were used to collect data, which were later exported to SPSS. Among 89 patients, more than 60% experienced crestal bone loss following implant placement. Diabetic patients recorded the highest prevalence of bone loss in comparison to other medically compromised patients. A significant association was found between crestal bone loss and diabetic patients (p < 0.05) Patients whose diseases were under control with medication were also observed to have bone loss. Overall, the prevalence of crestal bone loss seems to be higher in diabetic patients compared to other medically compromised patients. There seems to be definite correlation between diabetes and crestal bone loss.