 When still in his early twenties, Day was involved in a scandal surrounding a horse named Old England, trained by his father and owned by John Gully.Old England was fancied for the 1845 Epsom Derby, but Day wagered heavily against the colt and was involved in a plot to "nobble" (deliberately injure) it at the Danebury stable.Gully discovered the scheme and reported the matter to the Jockey Club.