sentence: records most successful horse ( 3 wins ) : underhand -- 1857 , 1858 , 1859 leading jockey since 1985 ( 2 wins ) : willie carson -- al maheb ( 1990 ) , celeric ( 1996 ) kevin darley -- far cry ( 1999 ) , bay of islands ( 2000 ) leading trainer since 1985 ( 3 wins ) : paul cole -- windsor castle ( 1997 ) , cyrian ( 1998 ) , archduke ferdinand ( 2001 ) winners since 1985 weights given in stone and pound .