 By the time of the Imperial Trans-Antarctic Expedition in 1914, the 48-year-old Cheetham was the crew member with most experience of the Antarctic, having spent almost six years in the seas around the continent

He was Third Officer on board the and was a popular and cheerful member of the crew.Frank Worsley refers to him as "a pirate to his fingertips".After "Endurance" was crushed in pack ice and the men set up for Elephant Island in the three lifeboats, he was part of Worsley's crew in the "Dudley Docker".