Future U. S. Racing Hall of Fame inductee Exterminator won the first three runnings of the Pimlico Cup beginning with the inaugural edition on November 13, 1919.
[3] The race of November 15, 1924, won by Altawood, was run in a snowstorm so heavy at times that the horses were barely visible and the colors undistinguishable.
Racing Hall of Fame inductee Horatio Luro and owned by the Mill River Stable of Josephine Douglas, won the 2+1⁄2 mile Pimlico Cup by forty lengths.
Nearing the finish, Jockey Conn McCreary eased Miss Grillo then stood up in the stirrups and waved to the crowd.
[6] Pilaster won the November 12, 1949, edition of the Pimlico Cup running temporarily under the name of trainer Frank Bonsal because owner Henry Lobe Straus had died in an October 25 airplane crash.