The April 24, 1920 inaugural brought together a field of six runners that included Harry Whitney's Wildair as well as the betting public's heavy favorite, an entry of Blazes and Paul Jones owned by Ral Parr.
However, the race saw a stunning upset by a 42:1 longshot named Sandy Beal who was skilfully ridden by future Hall of Fame jockey James Butwell.
[11] The 1934 Chesapeake Stakes was won Cavalcade who defeated future Hall of Fame inductee Discovery in a new track record time for a mile and one-sixteenth of 1:43 3/5.
[12] Owned by the Brookmeade Stable of automobile heiress Isabel Dodge Sloane, Cavalcade was the second Chesapeake winner to go on to win the Kentucky Derby in which he beat Discovery for the second straight time.
[14] A colt named War Admiral liked racing at the Havre de Grace track having won the 1936 Eastern Shore Handicap by five lengths in stakes record time.
Calumet Farm's Citation had lost his regular jockey when Albert Snider and two horse racing industry associates disappeared on March 5, 1948, during a sudden tropical storm while fishing in the Florida Keys.
[22] With replacement jockey Eddie Arcaro aboard, Citation was beaten by Saggy in the 1948 Chesapeake Trial that ended the colt's seven-race win streak.
Owned by the Greentree Stables of Helen Hay Whitney, Capot would have a great three-year-old campaign in which he won the 1949 Preakness and Belmont Stakes.