| 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 |
*—In 1897 The Squire, owned and ridden by W. Plunket Stewart, finished first but was disqualified for cutting a flag.
**—In 1923 Oracle II, owned by Mrs. M.M. Maddux and ridden by Raymond Belmont, finished first but was disqualified for cutting a flag.
***—In 1948 Carolina, owned by Henry Cadwalader and ridden by E.H. Bennett, was disqualified for jumping the wrong fence the second turn of the course.
****In 2015 Imperial Way, owned by Merriefield Farm and ridden by Bethany Baumgardner, finished first but was disqualified for losing the weight pad at the 19th fence and failing to weigh in at the required 165 lbs.
Course record of 8:22.60 was set by Vintage Vinnie (Ire) in 2021.
First challenge cup retired by Mrs. E. Read Beard 1940 (Blockade); second challenge cup retired by Stuart S. Janney Jr. 1947 (Winton); third challenge cup retired by Mrs. W.J. Clothier 1952 (Pine Pep); fourth challenge cup retired by Mrs. M.C. Stephenson 1966 (Jay Trump); fifth challenge cup retired by Redmond C. Stewart Jr. 1978 (Haffaday, Ben Nevis II); sixth challenge cup retired by Mrs. Miles Valentine 1983 (Cancottage); seventh challenge cup retired by Irvin L. Crawford II 2019 (Senior Senator).
