The aim of this study was to define the incidence and investigate the associations with mortality and medical complications, in patients presenting with subtrochanteric femoral fractures subsequently treated with an intramedullary nail, with a special reference to advancement of age. Materials and Methods: A retrospective review, covering an 8-year period, of all patients admitted to a Level 1 Trauma Centre with the diagnosis of subtrochanteric fractures was conducted. Normality was assessed for the data variables to determine the further use of parametric or non-parametric tests. Logistic regression analysis was then performed to identify the most important associations for each event. A p-value < 0.05 was considered significant. Results: A total of 519 patients were included in our study (age at time of injury: 73.26 ± 19.47 years; 318 female). The average length of hospital stay was 21.4 ± 19.45 days. Mortality was 5.4% and 17.3% for 30 days and one year, respectively. Risk factors for one-year mortality included: Low albumin on admission (Odds ratio (OR) 4.82; 95% Confidence interval (95%CI) 2.08–11.19), dementia (OR 3.99; 95%CI 2.27–7.01), presence of pneumonia during hospital stay (OR 3.18; 95%CI 1.76–5.77) and Charlson comorbidity score (CCS) > 6 (OR 2.94; 95%CI 1.62–5.35). Regarding the medical complications following the operative management of subtrochanteric fractures, the overall incidence of hospital acquired pneumonia (HAP) was 18.3%. Patients with increasing CCS (CCS 6–8: OR 1.69; 95%CI 1.00–2.84/CCS > 8: OR 2.02; 95%CI 1.03–3.95), presence of asthma/chronic obstructive pulmonary disease (COPD) (OR 2.29; 95%CI 1.37–3.82), intensive care unit (ICU)/high dependency unit (HDU) stay (OR 3.25; 95%CI 1.77–5.96) and a length of stay of more than 21 days (OR 8.82; 95%CI 1.18–65.80) were at increased risk of this outcome. The incidence of post-operative delirium was found to be 10.2%. This was associated with pre-existing dementia (OR 4.03; 95%CI 0.34–4.16), urinary tract infection (UTI) (OR 3.85; 95%CI 1.96–7.56), need for an increased level of care (OR 3.16; 95%CI 1.38–7.25), pneumonia (OR 2.29; 95%CI 1.14–4.62) and post-operative deterioration of renal function (OR 2.21; 95%CI 1.18–4.15). The incidence of venous thromboembolism (VTE) was 3.7% (pulmonary embolism (PE): 8 patients; deep venous thrombosis (DVT): 11 patients), whilst the incidence of myocardial infarction (MI)/cerebrovascular accidents (CVA) was 4.0%. No evidence of the so called “weekend effect” was identified on both morbidity and mortality. Regression analysis of these complications did not reveal any significant associations. Conclusions: Our study has opened the field for the investigation of medical complications within the subtrochanteric fracture population. Early identification of the associations of these complications could help prognostication for those who are at risk of a poor outcome. Furthermore, these could be potential “warning shots” for clinicians to act early to manage and in some cases prevent these devastating complications that could potentially lead to an increased risk of mortality.