Bentley's cars earned widespread acclaim for durability from the outset, competing in hill climbs and at Brooklands from the earliest years of production. The company's first major international event was the 1922 Indianapolis 500, where works driver Douglas Hawkes, accompanied by riding mechanic H. S. "Bertie" Browning, drove a modified Bentley road car to a 13th-place finish, completing the full 500 miles at an average of 74.95 miles per hour after starting 19th. The team then returned immediately to England to compete in the 1922 RAC Tourist Trophy on the Isle of Man.
The pivotal moment in Bentley's motorsport story came in 1924, when John Duff and Frank Clement took overall victory at the 24 Hours of Le Mans in a 3-litre Bentley. This win inspired Woolf Barnato — who had inherited a fortune from his father's South African gold and diamond mining interests — to invest in Bentley, injecting over £100,000 into the company in May 1926, saving it from financial collapse and becoming chairman.
Barnato's backing enabled the formation of the Bentley Boys, a group of wealthy and adventurous British motoring enthusiasts who drove Bentley works and private entries in competition through the late 1920s. The group included Barnato himself, Sir Henry "Tim" Birkin, steeple chaser George Duller, aviator Glen Kidston, automotive journalist S.C.H. "Sammy" Davis, and Dudley Benjafield. Many were independently wealthy and had military backgrounds.
Bentley achieved four consecutive Le Mans victories from 1927 to 1930. The company's Le Mans record in full:
1923: 4th (private entry, 3-litre)
1924: 1st (3-litre, works entry)
1927: 1st, 15th, 17th (3-litre)
1928: 1st, 5th (4½-litre)
1929: 1st (Speed Six); 2nd, 3rd, 4th (4½-litre)
1930: 1st, 2nd (Speed Six)
The dominant car of 1929 and 1930 was the Bentley Speed Six, a lighter-weight 6½-litre model introduced in 1928. It produced a remarkable 1-2-3-4 finish at Le Mans in 1929 and a 1-2 the following year.
Birkin developed a supercharged variant of the 4½-litre car at Welwyn Garden City in 1929, producing five racing specials. W. O. Bentley was vehemently opposed to the project, stating that to supercharge his engine was to "pervert its design and corrupt its performance." Barnato overruled him, and Birkin purchased 50 4½-litre cars to fulfil the homologation requirement, adding superchargers in his own workshop.
As W. O. Bentley predicted, the Blower Bentley proved fast but unreliable: no Blower Bentley ever won a race. Nevertheless, Birkin drove a stripped-down racing version to second place at the 1930 French Grand Prix at Pau, behind Philippe Etancelin in a Bugatti Type 35.
In March 1930, Barnato wagered £100 that he could race from Cannes to London in his 6½-litre Speed Six and arrive in London before Le Train Bleu, the famous French express, reached Calais. He drove on public roads from Cannes to Calais, crossed by ferry to Dover, and then continued to his London club, winning the wager comfortably. A painting by Terence Cuneo later depicted the race, though the scene it showed — the car racing parallel to the train — was fictional, as the road and railway routes did not run alongside each other.
Bentley withdrew from motor racing after the 1930 Le Mans, issuing a statement that they had "learned enough about speed and reliability." The financial pressure of the Great Depression followed: in July 1931 the company entered receivership and was acquired by Rolls-Royce, which operated via a front entity to conceal its identity during the purchase process.
After decades without a factory works programme, Bentley returned to top-level motorsport with victories at the 24 Hours of Le Mans in 2001 and 2003. In 2014, a Bentley Continental GT3 entered by the M-Sport factory team won the Silverstone round of the Blancpain Endurance Series — described as Bentley's first official entry in a British race since the 1930 RAC Tourist Trophy.
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