Racing as a juvenile, his best result in a major race was as runner-up in the Tremont Stakes. As a three-year-old, at Morris Park Racecourse in The Bronx, New York, Bowling Brook handily won the 1898 Metropolitan Handicap[2] then three weeks later at the same track, jockey Fred Littlefield rode him to victory in the 1 3/8 miles Belmont Stakes. Bowling Brook won on a muddy track by six lengths over the Mike Dwyer-owned and Tod Sloan-ridden colt Previous with Hamburg approximately another ten lengths back in third place. Owned by Marcus Daly and ridden by Fred Taral, future U.S. Racing Hall of Fame inductee Hamburg had been the betting favorite to win.
Stud career
Retired to stud duty, Bowling Brook met with limited success as a sire.