Purchased at age two in 1918 by owner/trainer John E. Madden, after winning the September 18th Hopeful Purse at Havre de Grace Racetrack he sold Milkmaid to Canadian, J.K.L.

During an illustrious career in which she was frequently ridden by the great Hall of Fame jockey, Earl Sande, Milkmaid won races at both sprint and longer distances.

On April 21, 1919, Milkmaid won the Wilmington Purse at Havre de Grace Racetrack, defeating a field of colts with Kentucky Derby and Preakness Stakes aspirations in a time that was just one-fifth of a second off the track record.

[3] A few weeks later on September 3, she set another track record against males in winning the Great Neck Handicap at a distance of a mile and a sixteenth at Belmont Park.

Retired to broodmare duty at her owner's Yarrow Brae Stud farm in Maryland, Milkmaid produced two foals from J.K. L. Ross's stallion, Cudgel.