May 30, Chris Anderson won a pair of races this week during the annual ankle in years past to win the annual Double Gloucester cheese-rolling race. May 29, The English county of Gloucestershire held its annual cheese rolling race Monday, and a bunch of people, whose bones were hopefully. Jun 1, A hilarious viral video captures crowds hurling themselves down a hill - and executing some spectacular tumbles - in pursuit of a wheel of. What is the Gloucester Cheese Rolling Competition? * Explained * Cooper's Hill Cheese Rolling Festival in Gloucestershire, south west England. dates back several hundred years validating the race as a world-famous event. The Cooper's Hill Cheese-Rolling and Wake is an annual event held on the Spring Bank a 9 pounds ( kilograms) round of Double Gloucester cheese is sent rolling down the hill, and competitors then start racing down the hill after it. May 30, The annual Cooper's Hill Cheese Roll competition in Brockworth, England, involves all-time record for the most cheeses won in Gloucestershire's death- defying races. Injuries at annual cheese rolling contest in UK.