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Trichilemmal carcinoma of scalp is a rare malignant tumour of scalp. A 52-year-old female presented with an extensive ulcerative lesion of the scalp. As the location of the tumour was in the occipital region and there was loss of bony skull in the region, this case became challenging. This patient was managed in the left lateral which was a difficult situation for even the experienced Anaesthesiologist. Intravenous access was acquired, central venous catheter (CVC) was placed in the right internal jugular vein under ultrasonography (USG) guidance and intubation was carried out in the lateral position. After the procedure, patient was again returned to the left lateral position. The trachea was extubated in the lateral position once the patient was awake, after thorough reversal of neuromuscular blockade. Patient had an uneventful postoperative period. This case report highlights the management of an unusual case of Trichilemmal carcinoma of the scalp.