Late in his two-year-old season he placed second in the Greenfield Stakes at Gravesend Race Track on Coney Island in south Brooklyn, New York.
Holiday, described as "a good-looking little bay gelding"[2] will best be remembered for his win in the $2,500 1914 Preakness Stakes at Pimlico Race Course in Baltimore, Maryland run on Thursday, May 21.
Holiday finished the classic in a final time of 1:58 flat under jockey Andy Schuttinger for the one and one eighth mile race.
[6] Later in his three-year-old season Holiday won the Williamsbridge Handicap at Morris Park Racecourse in Westchester County, New York.
In the early part of his four-year-old season Holiday was wintered at Fair Grounds Race Course in New Orleans, Louisiana.