One-Lung Ventilation (OLV) is achieved in thoracic surgeries to facilitate collapse of one lung for better surgical visualisation. Double-lumen tubes and bronchial blockers are two commonly used devices for OLV. Patients with ‘difficult airway’ pose significant challenges for insertion of Double Lumen Endotracheal Tube (DLT). Dual malignancy such as carcinoma of lung and head and neck is extremely rare to present with. Patients presenting with restricted mouth opening due to previous surgeries and requiring lung isolation techniques may pose significant challenges to anaesthesiologist. The difficult airway scenario may arise in such patients owing to their previous surgery to the tongue, larynx, neck, mandible or previous radiation. The present case was of 47-year-old of lung isolation achieved in a patient with restricted mouth opening with an orotracheal tube, bougie, endobronchial blocker and a flexible Fibre Optic Bronchoscope (FOB). Left upper lobectomy was successfully performed after passing endobronchial blocker through a conventional orotracheal tube under the guidance of FOB.