After she was purchased by the Dwyers, Miss Woodford, like Hindoo, was trained by National Museum of Racing and Hall of Fame inductee James G. Rowe Sr. A dispute with the Dwyers concerning Miss Woodford caused Rowe to resign and become a racing official.

At the time they acquired Miss Woodford, the Dwyer brothers already owned a colt who was considered the best of his crop.

One of the highlights of her three-year-old season was defeating George Kinney, her stablemate who had won the Belmont Stakes.

By the end of her fifth year of racing, Miss Woodford was America's leading money winner, having earned $98,179.

Miss Woodford won to push her earnings over the $100,000 mark, becoming the first horse ever to do so in a racing career.

Miss Woodford was inducted into the National Museum of Racing and Hall of Fame in Saratoga Springs, New York, in 1967.

Hall of Fame trainers Sunny Jim Fitzsimmons, Thomas J. Healey, A. Jack Joyner, R. Wyndham Walden, and Rowe all thought her one of the best fillies of all time.