Introduction: Health-Related Quality of Life (HRQOL) is a key indicator of how chronic conditions such as type 2 diabetes (T2D) affect an individual’s overall well-being. This study explored the relationship between HRQOL and health-related data in older T2D participants. Methods: This retrospective study analyzed data from 987 participants with T2D who underwent checkups at the IRCCS INRCA Hospital, Ancona, Italy. Participants with an EQ-5D-3L index score of 1 were classified as having “no problems” in any dimension, and those with a value less than 1 were categorized as having “any problems”. Results: The mean age was 76.5 years (SD ± 4.5), and 46.5% were male. The “any problems” group (n = 795) was older and had longer diabetes duration, lower educational attainment, higher total cholesterol, higher triglycerides, and a higher Body Mass Index (BMI) with respect to the “no problems” group (n = 195). Multivariate logistic regression identified female sex (OR 2.14, 95% CI: 1.24–3.70), higher BMI (OR 1.07, 95% CI: 1.01–1.14), and depressive symptoms by the 5-item mini-Geriatric Depression Scale (mini GDS 5) (OR 2.43, 95% CI: 1.84–3.21) as significantly associated with lower HRQOL. Conversely, higher scores of the Instrumental Activities of Daily Living (IADL) (OR 0.77, 95% CI: 0.65–0.91) were related to better HRQOL. Conclusions: Female sex, overweight status, depressive symptoms, and lower physical performance are associated with impaired HRQOL in older Italian T2D outpatients. In particular, the EQ-5D-3L index provides a comprehensive index associated with depressive symptoms and low mobility.