Oulton Park. Barely 17, he finished in 11th place, but was soon posting successful results. In 1958, he teamed with Dan Shorey to win the Thruxton 500 endurance race. By 1961, Hailwood was racing for an up and coming Japanese factory named Honda. Riding a four-stroke, four-cylinder 250 cc Honda, Hailwood won the 1961 250cc world championship. In 1962, Hailwood signed with MV Agusta and went on to become the first rider to win four consecutive 500cc World Championships. After his success with MV Agusta, Hailwood went back to Honda and won four more world titles in 1966 and 1967 in the 250 cc and 350 cc categories.
Silverstone racecourse on a BSA Lightning Clubman in heavy rain, beating the Triumph Racing Team's Bonnevilles. The 'Hutch' was the main production race of the season, so it was very important to manufactureres to establish the racing credentials of their latest range. Triumph Bonnevilles were ridden by World Champion Phil Read and ex works rider Percy Tait. BSA Lightning Clubmans were ridden by Hailwood (with a large number 1 on the fairing) and factory rider Tony Smith. Conditions were poor and Smith was out of the race at slippery Stowe Corner. With little regard for the rain, Hailwood was achieving laps of 83 mph (134 km/h) to establish his winning lead.
Hailwood is remembered for his accomplishments at the famed Isle of Man TT. By 1967, he had won 12 times on the island mountain course including three straight wins during the 1961 event, losing the fourth when his 350 AJS broke down with a broken gudgeon pin whilst leading. He won what many historians consider to be the most dramatic Isle of Man race of all time, the 1967 Senior TT against his great rival, Giacomo Agostini. In that race he set a lap record of 108.77 mph on the infamous Honda 500-4, that stood for the next 8 years.
On June 3, 1978, after an 11 year hiatus from motorcycling, Hailwood performed a now legendary comeback at the Isle of Man TT. Few observers believed the 38-year-old would be competitive after such a long absence. Riding a Ducati 900SS, he was not only competitive, but managed a hugely popular win. He raced the following year at the Isle of Man TT before retiring for good at the age of 39. In that final Isle of Man appearance, Hailwood rode a two-stroke Suzuki RG500 to victory in the Senior TT. He then opted to use that same 500cc bike in the Unlimited Classic and diced for the lead with Alex George (1100cc Honda) for all 6 laps in yet another TT epic. A minute or two apart on the road, they were rarely a few seconds apart on time each lap, Hailwood losing by just 2 seconds.
Here was a rider from the 'old-school' (he was the first to complete all 6 laps of the magnificent yet notorious Mountain Circuit at over 100mph on a single cylinder 500cc machine) coming to terms with vastly different machinery after 11 years away - the tyres, frame, brakes and engine power having undergone a quantum leap in capability, even the full-face helmet and brightly coloured padded leathers must have seemed strange - and yet still being able to get as a much from it as any rider around.
In 1968, Honda pulled out of Grand Prix racing, but paid Hailwood £50,000 (equivalent to over £620,000 or US$1.1m at 2006 prices) not to ride for another team, in expectation of keeping him as its rider upon return to competition. With no other factory racing teams available to compete against MV Agusta, Hailwood decided to pursue a career in auto racing.