Everything changed in 1902 when he met Henry Ford, who had prepared two race cars which were knows as the 999 and the Arrow. Oldfield was asked if he would like to drive one and he agreed. When he got to Grosse Point, Michigan, to test the cars, neither would start, so Henry Ford sold both to Oldfield and Tom Cooper for $800.
Barney Oldfield had never driven a motor vehicle of any kind prior to his first run in the 999. That was about a week before the race. There were four cars in the race but nobody could stay with Oldfield. He won easily with a time of five minutes, 28 seconds, which set a record for a five-mile race on a closed course. Soon Cooper and Oldfield were touring the country with the 999 and Arrow, winning races and setting speed records. In the summer of 1903, Oldfield raced the Ford 999 around the Indiana Fairgrounds one-mile dirt track at 60 mph, the fastest speed ever recorded on a closed circuit.
In 1903 Barney Oldfield joined the George Winton’s team. Winton, who was a prominent auto builder and racer, offered Oldfield salary and cars to race. Oldfield’s criss-crossed the country in a series of match races and speed runs. His showmanship came to the forefront. Oldfield delighted fair-goers with interminable record-breaking. He even appeared on stage in a play about racing in which he portrayed a poor mechanic who saves the day. In 1910, Oldfield bought a Benz with which he broke all existing speed records for the mile, two miles and the kilometer in special runs at Ormond Beach.
Barney Oldfield also competed at Indianapolis. His best finishes were fifth in 1914 and 1916. However, speed records, match races and exhibitions made up most of Oldfield’s career. The cigar-chomping speed merchant was such a star he was in almost constant demand. Barney Oldfield retired from racing in 1918, but continued to tour, make movies and tended to racing business. Barney Oldfield died on October 4, 1946.