| PAST WINNERS OF THE MARYLAND HUNT CUP | |||
| Year | Winner | Owner | Rider |
| 1894 | JOHNNY MILLER | John McHenry | John McHenry |
| 1895 | SIXTY | Samuel E. George | R. N. Elder Jr. |
| 1896 | KINGSBURY | Mrs. Thomas D. Whistler | Thomas D. Whistler |
| 1897 | LITTLE GIANT* | Charles R. Spence | George Elder |
| 1898 | THE SQUIRE | W. Plunket Stewart | W. Plunket Stewart |
| 1899 | REVELLER | James Piper | James Piper |
| 1900 | TOM CLARK | George Brown Jr. | George Brown Jr. |
| 1901 | GARRY OWEN | J. H. O’Donovan | Jervis Spencer Jr. |
| 1902 | GARRY OWEN | J. H. O’Donovan | Jervis Spencer Jr. |
| 1903 | PRINCETON | W. J. H. Watters | W. J. H. Watters |
| 1904 | LANDSLIDE | Redmond C. Stewart | Redmond C. Stewart |
| 1905 | PRINCETON | Sidney Watters | Sidney Watters |
| 1906 | PRINCETON | W. J. H. Watters | W. J. H. Watters |
| 1907 | GARRY OWEN | J. H. O’Donovan | Jervis Spencer Jr. |
| 1908 | JUDGE PARKER | James Piper | George Nicholas |
| 1909 | SACANDAGA | Miss Frances Fell | Alfred Devereux |
| 1910 | SACANDAGA | Mrs. A. J. A. Devereux | A. J. A. Devereux |
| 1911 | PEBBLES | Alexander Brown | J. G. Leiper Jr. |
| 1912 | CONBE | George Blakiston Jr. | T. Buchanan Blakiston |
| 1913 | ZARDA | George Willing Jr. | Allen Lee |
| 1914 | RUTLAND | Brandywine Stables | Gilbert Mather |
| 1915 | TALISMAN | Allan Pinkerton | Jervis Spencer Jr. |
| 1916 | BURGEOIS | J. S. Wilson Jr. | George Brown Jr. |
| 1917 | BROSSEAU | William J. Clothier | Gilbert Mather |
| 1918 | MARCELLINUS | W. Plunket Stewart | E. M. Cheston |
| 1919 | CHUCKATUCK | B. H. Brewster Jr. | Jervis Spencer Jr. |
| 1920 | ORACLE II | Mrs. M. M. Maddux | Arthur White |
| 1921 | MAZARIN | Mrs. R. C. Stewart | Gough W. Thompson |
| 1922 | ORACLE II | Mrs. M. M. Maddux | Raymond Belmont |
| 1923 | RED BUD** | William Almy Jr. | Crawford Burton |
| 1924 | DAYBREAK | Joseph Neff Ewing | Joseph Neff Ewing |
| 1925 | BURGORIGHT | Benjamin Leslie Behr | Joseph T. Bowen Jr. |
| 1926 | BILLY BARTON | Howard Bruce | Albert G. Ober Jr. |
| 1927 | BON MASTER | C. L. A. Heiser | Frank A. Bonsal |
| 1928 | BON MASTER | C. L. A. Heiser | Frank A. Bonsal |
| 1929 | ALLIGATOR | Mrs. M. K. Stevenson | Charles D. Plumb |
| 1930 | BROSE HOVER | Benjamin Leslie Behr | Crawford Burton |
| 1931 | SOISSONS | Flying Horse Farm | John T. Skinner |
| 1932 | TROUBLE MAKER | Mrs. T. H. Somerville | Noel Laing |
| 1933 | CAPTAIN KETTLE | Charles S. Cheston | Charles R. White |
| 1934 | CAPTAIN KETTLE | Charles S. Cheston | Charles R. White |
| 1935 | HOTSPUR II | Mrs. W.A. Wadsworth | Stuart S. Janney Jr. |
| 1936 | INSHORE | J. W. Y. Martin | Henry W. Frost Jr. |
| 1937 | WELBOURNE JAKE | Paul Mellon | John Harrison |
| 1938 | BLOCKADE | Mrs. E. Read Beard | J. Fred Colwill |
| 1939 | BLOCKADE | Mrs. E. Read Beard | J. Fred Colwill |
| 1940 | BLOCKADE | Mrs. E. Read Beard | J. Fred Colwill |
| 1941 | COQ BRUYERE | John Strawbridge | R. P. Hamilton |
| 1942 | WINTON | Stuart S. Janney Jr. | Stuart S. Janney Jr. |
| 1943, 1944, 1945, race not held because of war | |||
| 1946 | WINTON | Stuart S. Janney Jr. | Stuart S. Janney Jr. |
| 1947 | WINTON | Stuart S. Janney Jr. | Stuart S. Janney Jr. |
| 1948 | PETERSKI*** | E. Q. McVitty | D. Michael Smithwick |
| 1949 | PINE PEP | Mrs. W. J. Clothier | D. Michael Smithwick |
| 1950 | PINE PEP | Mrs. W. J. Clothier | D. Michael Smithwick |
| 1951 | JESTER’S MOON | Mrs. J. Strawbridge Jr. | William H. Dixon |
| 1952 | PINE PEP | Mrs. W. J. Clothier | D. Michael Smithwick |
| 1953 | THIRD ARMY | Harry A. Love | P. D. Reid |
| 1954 | MARCHIZED | Miss Cynthia Cannon | D. Michael Smithwick |
| 1955 | LAND’S CORNER | Mrs. W. J. Strawbridge | B. H. Murray |
| 1956 | LANCREL | Hugh J. O’ Donovan | Frank A. Bonsal Jr. |
| 1957 | NED’S FLYING | Mrs. C. P. Denckla | Eugene Weymouth |
| 1958 | NED’S FLYING | Mrs. C. P. Denckla | Philip F. N. Fanning |
| 1959 | FLUCTUATE | H. Robertson Fenwick | Crompton Smith Jr. |
| 1960 | FLUCTUATE | H. Robertson Fenwick | D. Michael Smithwick |
| 1961 | SIMPLE SAMSON | Bliss Flaccus | Crompton Smith Jr. |
| 1962 | MOUNTAIN DEW | Janon Fisher Jr. | Janon Fisher III |
| 1963 | JAY TRUMP | Mrs. M. C. Stephenson | Crompton Smith Jr. |
| 1964 | JAY TRUMP | Mrs. M. C. Stephenson | Crompton Smith Jr. |
| 1965 | MOUNTAIN DEW | Janon Fisher Jr. | Janon Fisher III |
| 1966 | JAY TRUMP | Mrs. M. C. Stephenson | Crompton Smith Jr. |
| 1967 | MOUNTAIN DEW | Janon Fisher Jr. | Janon Fisher III |
| 1968 | HAFFADAY | Redmond C. Stewart Jr. | Louis Neilson III |
| 1969 | LANDING PARTY | John R. S. Fisher | John R. S. Fisher |
| 1970 | MORNING MAC | Mrs. John B. Hannum | R. P. S. Hannum |
| 1971 | LANDING PARTY | John R. S. Fisher | John R. S. Fisher |
| 1972 | EARLY EARNER | J. W. Y. Martin Jr. | J. W. Y. Martin Jr. |
| 1973 | MORNING MAC | Mrs. John B. Hannum | R. P. S. Hannum |
| 1974 | BURNMAC | Mrs. E. E. Weymouth | Louis Neilson III |
| 1975 | JACKO | Shiloh Farm | Russell B. Jones Jr. |
| 1976 | FORT DEVON | Charles S. Bird Jr. | R. P. S. Hannum |
| 1977 | BEN NEVIS II | Redmond C. Stewart Jr. | Charles C. Fenwick Jr. |
| 1978 | BEN NEVIS II | Redmond C. Stewart Jr. | Charles C. Fenwick Jr. |
| 1979 | DOSDI | Mrs. Donald M. Culver | Charles C. Fenwick Jr. |
| 1980 | CANCOTTAGE | Mrs. Miles Valentine | Joy Slater |
| 1981 | CANCOTTAGE | Mrs. Miles Valentine | Joy Slater |
| 1982 | TONG | H. Turney McKnight | H. Turney McKnight |
| 1983 | CANCOTTAGE | Mrs. Miles Valentine | Charles C. Fenwick Jr. |
| 1984 | BEWLEY’S HILL | Mrs. W. B. D. Stroud Jr. | W. B. Dixon Stroud Jr. |
| 1985 | OUR STEEPLEJACK | Mrs. W. A. Speakman | John M. Bosley |
| 1986 | TONG | H. Turney McKnight | Elizabeth P. McKnight |
| 1987 | SUGAR BEE | Arthur W. Arundel | Charles C. Fenwick Jr. |
| 1988 | FREEMAN’S HILL | Foxbrook Farm | William Meister |
| 1989 | UNCLE MERLIN | Mrs. Roy Chapman | Louis Neilson III |
| 1990 | THE HARD WORD | Quartet Stables | William Meister |
| 1991 | TOM BOB | Fat Chance Farm | Sanna Neilson |
| 1992 | VON CSADEK | Sheppard-Worrall Stable | Patrick Worrall |
| 1993 | IVORY POACHER | Landslide Farm | Sanna Neilson |
| 1994 | REVELSTOKE | Mrs. John R. S. Fisher | Jack Fisher |
| 1995 | BUCK JAKES | Arcadia Stable | Anne K. Moran |
| 1996 | HELLO HAL | Club Hal Stables | William Meister |
| 1997 | BUCK JAKES | Arcadia Stable | Anne K. Moran |
| 1998 | FLORIDA LAW | Bachelors’ Hall | Joseph Davies Gillet |
| 1999 | Welter Weight | Armata Stables | Mike Elmore |
| 2000 | SWAYO | Move Up Stable | Joseph Davies Gillet |
| 2001 | SOLO LORD | Michael E. Hoffman | Michael E. Hoffman |
| 2002 | YOUNG DUBLINER (Ire) | William C. Lickle | Brian Moran |
| 2003 | SWAYO | Move Up Stable | Chris Gracie |
| 2004 | BUG RIVER | Northwoods Stable | Blair Waterman |
| 2005 | MAKE ME A CHAMP | Irvin S. Naylor | Joseph Gillet Davies |
| 2006 | BUG RIVER | Northwoods Stable | Chris Gracie |
| 2007 | THE BRUCE (NZ) | Stewart Strawbridge | Stewart Strawbridge |
| 2008 | ASKIM (NZ) | Irvin S. Naylor | Charles C. Fenwick III |
| 2009 | MICHELE MARIESCHI (GB) | Anna Stable | George Hundt Jr. |
| 2010 | TWILL DO | Lucy Goelet | James Stierhoff |
| 2011 | PRIVATE ATTACK | Sportsmans Hall | Blythe Miller Davies |
| 2012 | TWILL DO | Lucy Goelet | James Stierhoff |
| 2013 | PROFESSOR MAXWELL | Mrs. George L. Ohrstrom Jr. | Mark Beecher |
| 2014 | GUTS FOR GARTERS | FOXY Stables | Jody Petty |
| 2015 | RAVEN’S CHOICE**** | Mrs. Cary W. Jackson | Mark Beecher |
| 2016 | SENIOR SENATOR | Irvin L. Crawford II | Eric Poretz |
| 2017 | DERWINS PROSPECTOR | Gerry L. Brewster | Gonzague Cottreau |
| 2018 | SENIOR SENATOR | Irvin L. Crawford II | Eric Poretz |
| 2019 | SENIOR SENATOR | Irvin L. Crawford II | Eric Poretz |
| 2021 | VINTAGE VINNIE (Ire) | Armata Stable | Dan Nevin |
| 2022 | VINTAGE VINNIE (Ire) | Armata Stable | Teddy Davies |
| 2023 | Withoutmoreado (Ire) | Irvin S. Naylor | Conor Tierney |
| 2024 | Blackhall (Ire) | Kinross Farm | Charlie Marshall |
| 2025 | Road to Oz | Daniel R. Baker | Conor Tierney |