Since 2005, the School has organised an annual ski trip to Canada in the Christmas holidays, with many Harrovians attending every year.

In the early days, more than 12 years ago, the trip organiser (Head of Army and School Staff Instructor Rob Robson) took seven boys to an Army adventure-training establishment near Canmore, Alberta, from where the boys had race training at Nakiska, a purpose-built racing arena that was used in the 1978 Olympics. Since 2007, the trip has taken place in Jasper; and it was in that year that Rob established the Canada Cup, the first of which Harrow won in a contest against Eton.

This year, a record 61 Harrovians - of all ages and representing each House - went on the 11-day trip. While most enjoyed recreational skiing and snowboarding, 26 undertook race training and three took their Level 1 instructors' course (one in skiing and two in snowboarding). There were ten beginners, many of whom were skiing black diamond runs by the end of the trip. The snow was excellent throughout and the skiers enjoyed five hours on the slopes each day. Other activities included a guided walk along the frozen Maligne Canyon, a cinema trip, an ice-hockey game, quizzes and avalanche awareness training.

The Canada Cup took place across two days, with some 120 racers from seven schools (Eton, Reeds, Dulwich, Wellington, Westminster, Tonbridge and Harrow) taking part in the tenth-anniversary event. While individual Harrovians took first, second and third places, the School narrowly lost the Cup to Reeds School, by 200th of a second. At the Cup's gala dinner, the Marmot Basin and Ski Club 500 hosted 350 guests. Prizes were presented by Old Harrovian William Mathews (The Park 1993).