Winners of The Massachusetts Handicap
| Year |
Winner |
Age |
Jockey |
Trainer |
Owner |
Time |
Grade |
| 2011 | No Race | ||||||
| 2010 | No Race | ||||||
| 2009 | No Race | ||||||
| 2008 | Commentator | 7 | John Velazquez | Nick Zito | Tracy Farmer | 1:48.97 | NG |
| 2007 | Brass Hat | 6 | Willie Martinez | William B. Bradley | Fred F. Bradley | 1:49.72 | NG |
| 2006 | No Race | ||||||
| 2005 | No Race | ||||||
| 2004 | Offlee Wild | 4 | Edgar Prado | Richard E. Dutrow, Jr. | AZ Azalea Stables LLC | 1:49.14 | II |
| 2003 | No Race | ||||||
| 2002 | Macho Uno | 4 | Gary L. Stevens | Joe Orseno | Stronach Stables | 1:50.52 | II |
| 2001 | Include | 4 | Jerry D. Bailey | Bud Delp | Robert E. Meyerhoff | 1:48.60 | II |
| 2000 | Running Stag | 6 | John Velazquez | Philip Mitchell | Richard J. Cohen | 1:49.45 | II |
| 1999 | Behrens | 5 | Jorge Chavez | H. James Bond | Rudlein Stable | 1:49.00 | II |
| 1998 | Skip Away | 5 | Jerry D. Bailey | Sonny Hine | Carolyn Hine | 1:47.27 | III |
| 1997 | Skip Away | 4 | Shane Sellers | Sonny Hine | Carolyn Hine | 1:47.80 | III |
| 1996 | Cigar | 6 | Jerry D. Bailey | William I. Mott | Allen E. Paulson | 1:49.60 | NG |
| 1995 | Cigar | 5 | Jerry D. Bailey | William I. Mott | Allen E. Paulson | 1:48.60 | NG |
| 1994 | No Race | ||||||
| 1993 | No Race | ||||||
| 1992 | No Race | ||||||
| 1991 | No Race | ||||||
| 1990 | No Race | ||||||
| 1989 | Private Terms | 4 | Kent Desormeaux | Charles H. Hadry | Locust Hill Farm | 1:49.40 | II |
| 1988 | Lost Code | 4 | Craig Perret | L. William Donovan | Wendover Stable | 1:50.20 | II |
| 1987 | Waquoit | 4 | Chris McCarron | Guido Federico | Joseph Federico | 1:49.00 | II |
| 1986 | Skip Trial | 4 | Jean-Luc Samyn | Sonny Hine | Zelda Cohen | 1:49.80 | II |
| 1985 | Bounding Basque | 5 | Antonio Graell | Woody Sedlacek | Jacques D. Wimpfheimer | 1:47.60 | II |
| 1984 | Dixieland Band | 4 | Declan Murphy | Charles Peoples | Mary Sharp | 1:52.00 | II |
| 1983 | Let Burn | 4 | Jack Penney | William W. Perry | Scorpio Stable | 1:48.80 | II |
| 1982 | Silver Supreme | 4 | Eric Beitia | Richard DeStasio | Michael Berry | 1:48.80 | III |
| 1981 | Soldier Boy | 5 | Roger Danjean | Dominique Imprescia | Sandy Cooperstein | 1:49.40 | III |
| 1980 | Ring of Light | 5 | Frank Lovato, Jr. | Pancho Martin | Viola Sommer | 1:50.40 | III |
| 1979 | Island Sultan | 4 | John Ruane | David Hofmans | Buckland Farm | 1:48.60 | II |
| 1978 | Big John Taylor | 4 | Jacinto Vasquez | Doug Peterson | Karen L. Taylor | 1:48.40 | II |
| 1977 | Blue Times | 6 | Angel Cordero, Jr. | Laz Barrera | Aaron U. Jones | 1:49.40 | II |
| 1977 | Swinging Hal | 4 | Steve Pagano | J. W. Woods | John Martin | 1:49.20 | II |
| 1976 | Dancing Champ | 4 | Chris McCarron | Bud Delp | Windfields Farm | 1:49.20 | II |
| 1975 | Stonewalk | 4 | Ron Turcotte | Daniel J. Lopez | Timberland Stable | 1:48.60 | II |
| 1974 | Billy Come Lately | 4 | Don MacBeth | D. Michael Smithwick | Richard W. Palmer | 1:48.60 | II |
| 1973 | Riva Ridge | 4 | Ron Turcotte | Lucien Laurin | Meadow Stable | 1:48.20 | II |
| 1972 | Droll Role | 4 | Eddie Maple | Thomas J. Kelly | John M. Schiff | 1:49.20 | |
| 1971 | Chompion | 6 | Jorge Velasquez | Ivor G. Balding | C. V. Whitney | 2:34.40 | |
| 1970 | Semillant | 5 | Jean Cruguet | Angel Penna, Sr. | Sarah Hall | 2:37.20 | |
| 1969 | Beau Marker | 4 | Leroy Moyers | Lucien Laurin | Reginald N. Webster | 2:04.60 | |
| 1968 | Out Of The Way | 3 | John L. Rotz | Max Hirsch | King Ranch | 2:02.80 | |
| 1967 | Good Knight | 5 | Karl Korte | Arnold Scruton, Jr. | Arnold Scruton | 2:02.40 | |
| 1966 | Fast Count | 3 | Mike Venezia | Ivor G. Balding | C. V. Whitney | 2:01.20 | |
| 1965 | Smart | 6 | Eldon Nelson | Henry S. Clark | Christiana Stable | 2:01.60 | |
| 1964 | Smart | 5 | Eldon Nelson | Henry S. Clark | Christiana Stable | 2:03.20 | |
| 1963 | Crimson Satan | 4 | Herberto Hinojosa | Gordon R. Potter | Crimson King Farm | 2:01.20 | |
| 1962 | Air Pilot | 8 | Leroy Moyers | Clyde Troutt | Ada L. Rice | 2:01.40 | |
| 1961 | Polylad | 5 | Eddie Arcaro | Thomas M. Miles | Mrs. Q. A. S. McKean | 2:01.80 | |
| 1960 | Talent Show | 5 | Ray Broussard | Clyde Troutt | Ada L. Rice | 2:03.60 | |
| 1959 | Air Pilot | 5 | Jack Leonard | Clyde Troutt | Ada L. Rice | 2:02.40 | |
| 1958 | Promised Land | 4 | Pete D. Anderson | Hirsch Jacobs | Ethel D. Jacobs | 2:01.80 | |
| 1957 | Greek Spy | 4 | Eric Guerin | Sherrill W. Ward | Charles U. Bay | 2:03.20 | |
| 1956 | Midafternoon | 4 | William Boland | Thomas M. Waller | Mrs. E. E. Robbins | 2:04.00 | |
| 1955 | Helioscope | 4 | Sam Boulmetis, Sr. | Frank Caltrone | William G. Helis, Jr. | 2:01.00 | |
| 1954 | Wise Margin | 4 | Keith Stuart | S. N. Edmundson | Sam Tufano | 2:01.60 | |
| 1953 | Royal Vale | 5 | Jack Westrope | James E. Ryan | Esther D. du Pont | 2:02.20 | |
| 1952 | To Market | 4 | William Boland | Max Hirsch | King Ranch | 2:01.40 | |
| 1951 | One Hitter | 5 | Ted Atkinson | John M. Gaver, Sr. | Greentree Stable | 2:02.20 | |
| 1950 | Cochise | 4 | Eddie Arcaro | Virgil W. Raines | Brandywine Stable | 2:01.80 | |
| 1949 | First Nighter | 4 | Joseph Renick | William J. Hirsch | Sam A. Mason II | 2:04.60 | |
| 1948 | Beauchef | 5 | Ruperto Donoso | Robert T. Odom | Andes Stable | 2:02.60 | |
| 1947 | Stymie | 6 | Conn McCreary | Hirsch Jacobs | Ethel D. Jacobs | 1:50.00 | |
| 1946 | Pavot | 4 | Arnold Kirkland | Oscar White | Walter M. Jeffords | 1:49.80 | |
| 1945 | First Fiddle | 6 | Johnny Longden | Eddie Mulrenan | Mrs. E. Mulrenan | 1:49.40 | |
| 1944 | First Fiddle | 5 | Johnny Longden | Eddie Mulrenan | Mrs. E. Mulrenan | 1:49.00 | |
| 1943 | Market Wise | 5 | Vincenzo Nodarse | George W. Carroll | Louis Tufano | 1:52.00 | |
| 1942 | Whirlaway | 4 | George Woolf | Ben A. Jones | Calumet Farm | 1:48.20 | |
| 1941 | War Relic | 3 | Ted Atkinson | Walter A. Carter | Glen Riddle Farm | 1:48.60 | |
| 1940 | Eight Thirty | 4 | Harry Richards | Bert Mulholland | George D. Widener, Jr. | 1:49.00 | |
| 1939 | Fighting Fox | 4 | James Stout | James Fitzsimmons | Belair Stud | 1:52.00 | |
| 1938 | Menow | 3 | Nick Wall | Duval A. Headley | Hal Price Headley | 1:52.60 | |
| 1937 | Seabiscuit | 4 | Red Pollard | Tom Smith | Charles S. Howard | 1:49.00 | |
| 1936 | Time Supply | 5 | Raymond Workman | Carl A. Roles | Mrs. Frank A. Carreaud | 1:49.80 | |
| 1935 | Top Row | 4 | George Woolf | Albert A. Baroni | Albert A. Baroni | 1:49.40 |
* Day Court finished first in 1959 but was disqualified and placed second.
* Raced in two divisions in 1977.
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Famous quotes containing the words winners and/or handicap:
“The two real political parties in America are the Winners and the Losers. The people don’t acknowledge this. They claim membership in two imaginary parties, the Republicans and the Democrats, instead.”
—Kurt Vonnegut, Jr. (b. 1922)
“I have the handicap of being born with a special language to which I alone have the key.”
—Gustave Flaubert (1821–1880)