Aim: The main purpose for a good management of the diabetic disease is to avoid blood glucose swings. This study aims to analyze the diabetic management focusing on iatrogenic hypoglycemia, the therapeutic failure and the Body Mass Index (BMI). Methods: Diabetic patients were divided into insulin/secretagogue drugs (insulin/SD), Glucagon Like Peptide-1 Receptor Agonist (GLP-1RA) and Dipeptidylpeptidase-4 inhibitors (DPP-4i). An algorithm was created to identify hypoglycemic events, considering fracture discharge, access to emergency for coma or driving mishaps, and Self- Monitoring Blood Glucose. The achievement of glycated hemoglobin (HbA1c) target level (≤ 7%) and BMI target (≤ 25 kg/m2) were analyzed as well. Results: 16.23% out of 16,549 patients had at least one hypoglycemic event. Patients taking insulin/SD (94.39%) had a major risk of hypoglycemia (OR=2.01 p<0.001), while the groups with GLP-1 RA (1.87%) and DPP-4i (3.47%) show an OR of 0.59 (p<0.001) and 0.44 (p<0.001), respectively. The therapeutic target of HbA1c was achieved only in patients treated with DPP-4i (6.85% p<0.001). The BMI remained over the target threshold both before and during treatment for all groups but increased only for patients with insulin/SD (from 29.29 to 29.58 kg/m2). The major decrease in the number of BMI off-target patients was reported for the DPP-4i group (86.2% and 80.1% before and during treatment). Conclusions: The DPP-4i treatment did not associate with hypoglycemia and allowed HbA1c target achievement. Insulin/SD therapy, in contrast, correlated with an increased risk of hypoglycemic events, weight gain, and failure to achieve hematic target with HbA1c.