Context: Postoperative pneumonia (POP) is a major cause of morbidity following upper abdominal oncological surgeries. Aims: To estimate the incidence of POP following upper abdominal oncological surgeries and to identify its clinical and microbiologic features and the risk factors for the development of severe pneumonia. Settings and Design: Retrospective analysis of patients with POP at a regional cancer center. Patients and Methods: Patients’ preoperative and intraoperative details and data on clinical and radiological features and pathogens isolated were collected. Patients with severe pneumonia were identified on the basis of Infectious Disease Society of America/American Thoracic Society criteria and their predictors were estimated. The types of respiratory support required and their outcomes were analysed. Statistical Analysis Used: Parametric Student's t-independent test was used to compare two groups’ means. Categorical data are presented as frequency and percentage values. P < 0.05 was considered statistically significant. Results: Incidence of POP was 15.24% with 48% developing severe pneumonia. There was a significant difference in the mean age (59.5 ± 8.62 vs. 50.15 ± 10.53 years, P = 0.024), duration of surgery (315.77 ± 107.29 vs. 432.92 ± 177.18 min, P = 0.055), blood loss (446.15 ± 260.18 ml vs. 712.5 ± 326.22 ml), time to empiric antibiotic (15.69 ± 5.77 vs. 42 ± 38.12 h, P = 0.022), and symptom resolution =3 days (23.1% vs. 72.7%) between patients with nonsevere and severe pneumonia. Patients presenting with cough (odds ratio = 0.06, 95% confidence interval: 0.006–0.618) were more likely to have nonsevere pneumonia. Conclusions: Predictors of severe pneumonia are elderly, prolonged surgical duration, higher blood loss, delayed empiric antibiotic and delayed symptom resolution.