| Year | Name | Home | Time |
| 1897 | John J. McDermott | New York | 2:55:10 |
| 1898 | Ronald J. McDonald | Canada | 2:42:00 |
| 1899 | Lawrence Brignolia | Massachusetts | 2:54:38 |
| 1900 | John Caffrey | Canada | 2:39:44 |
| 1901 | John Caffrey | Canada | 2:29:23 |
| 1902 | Sammy Mellor | New York | 2:43:12 |
| 1903 | John Lorden | Massachusetts | 2:41:29 |
| 1904 | Michael Spring | New York | 2:38:04 |
| 1905 | Frederick Lorz | New York | 2:38:25 |
| 1906 | Tim Ford | Massachusetts | 2:45:45 |
| 1907 | Thomas Longboat | Canada | 2:24:24 |
| 1908 | Thomas Morrisey | New York | 2:25:43 |
| 1909 | Henri Renaud | New Hampshire | 2:53:36 |
| 1910 | Fred Cameron | Canada | 2:28:52 |
| 1911 | Clarence DeMar | Massachusetts | 2:21:39 |
| 1912 | Michael Ryan | New York | 2:21:18 |
| 1913 | Fritz Carlson | Minnesota | 2:25:14 |
| 1914 | James Duffy | Canada | 2:25:01 |
| 1915 | Edouard Fabre | Canada | 2:31:41 |
| 1916 | Arthur Roth | Massachusetts | 2:27:16 |
| 1917 | Bill Kennedy | New York | 2:28:37 |
| 1918 | Special Military Relay | Camp Devens | 2:29:53 |
| 1919 | Carl Linder | Massachusetts | 2:29:13 |
| 1920 | Peter Trivoulides | New York | 2:29:31 |
| 1921 | Frank Zuna | New York | 2:18:57 |
| 1922 | Clarence DeMar | Massachusetts | 2:18:10 |
| 1923 | Clarence DeMar | Massachusetts | 2:23:47 |
| 1924 | Clarence DeMar | Massachusetts | 2:29:40 |
| 1925 | Charles Mellor | Illinois | 2:33:00 |
| 1926 | John C. Miles | Canada | 2:25:40 |
| 1927 | Clarence DeMar | Massachusetts | 2:40:22 |
| 1928 | Clarence DeMar | Massachusetts | 2:37:07 |
| 1929 | John C. Miles | Canada | 2:33:08 |
| 1930 | Clarence DeMar | Massachusetts | 2:34:48 |
| 1931 | James P. Henigan | Massachusetts | 2:46:45 |
| 1932 | Paul DeBruyn | Germany | 2:33:36 |
| 1933 | Leslie S. Pawson | Rhode Island | 2:31:01 |
| 1934 | Dave Komonen | Canada | 2:32:53 |
| 1935 | John A. Kelley | Massachusetts | 2:32:07 |
| 1936 | Ellison M. Brown | Rhode Island | 2:33:40 |
| 1937 | Walter Young | Canada | 2:33:20 |
| 1938 | Leslie S. Pawson | Rhode Island | 2:35:34 |
| 1939 | Ellison M. Brown | Rhode Island | 2:28:51 |
| 1940 | Gerard Cote | Canada | 2:28:28 |
| 1941 | Leslie S. Pawson | Rhode Island | 2:30:38 |
| 1942 | Joe Smith | Massachusetts | 2:26:51 |
| 1943 | Gerard Cote | Canada | 2:28:25 |
| 1944 | Gerard Cote | Canada | 2:31:50 |
| 1945 | John A. Kelley | Massachusetts | 2:30:40 |
| 1946 | Stylianos Kyriakides | Greece | 2:29:27 |
| 1947 | Yun Bok Suh | Korea | 2:25:39 |
| 1948 | Gerard Cote | Canada | 2:31:02 |
| 1949 | Karl Leandersson | Sweden | 2:31:50 |
| 1950 | Kee Yong Ham | Korea | 2:32:39 |
| 1951 | Shigeki Tanaka | Japan | 2:27:45 |
| 1952 | Doroteo Flores | Guatamela | 2:31:53 |
| 1953 | Keizo Yamada | Japan | 2:18:51 |
| 1954 | Veikko Karvonen | Finland | 2:20:39 |
| 1955 | Hideo Hamamura | Japan | 2:18:22 |
| 1956 | Antti Viskari | Finland | 2:14:14 |
| 1957 | John J. Kelley | Connecticut | 2:20:05 |
| 1958 | Franjo Mihalic | Yugoslavia | 2:25:54 |
| 1959 | Eino Oksanen | Finland | 2:22:42 |
| 1960 | Paavo Kotila | Finland | 2:20:54 |
| 1961 | Eino Oksanen | Finland | 2:23:29 |
| 1962 | Eino Oksanen | Finland | 2:23:48 |
| 1963 | Aurele Vandendriessche | Belgium | 2:18:58 |
| 1964 | Aurele Vandendriessche | Belgium | 2:19:59 |
| 1965 | Morio Shigematsu | Japan | 2:16:33 |
| 1966 | Kenji Kemihara | Japan | 2:17:11 |
| 1967 | David McKenzie | New Zealand | 2:15:45 |
| 1968 | Amby Burfoot | Connecticut | 2:22:17 |
| 1969 | Yoshiaki Unetani | Japan | 2:13:49 |
| 1970 | Ron Hill | Great Britain | 2:10:30 |
| 1971 | Alvaro Mejia | Colombia | 2:18:45 |
| 1972 | Olavi Suomalainen | Finland | 2:15:39 |
| 1973 | Jon Anderson | Oregon | 2:16:03 |
| 1974 | Neal Cusack | Ireland | 2:13:39 |
| 1975 | Bill Rodgers | Massachusetts | 2:09:55 |
| 1976 | Jack Fultz | Virginia | 2:20:19 |
| 1977 | Jerome Drayton | Canada | 2:14:46 |
| 1978 | Bill Rodgers | Massachusetts | 2:10:13 |
| 1979 | Bill Rodgers | Massachusetts | 2:09:27 |
| 1980 | Bill Rodgers | Massachusetts | 2:12:11 |
| 1981 | Toshihiko Seko | Japan | 2:09:26 |
| 1982 | Alberto Salazar | Massachusetts | 2:08:52 |
| 1983 | Greg Meyer | Massachusetts | 2:09:00 |
| 1984 | Geoff Smith | Great Britain | 2:10:34 |
| 1985 | Geoff Smith | Great Britain | 2:14:05 |
| 1986 | Robert de Castella | Australia | 2:07:51 |
| 1987 | Toshihiko Seko | Japan | 2:11:50 |
| 1988 | Ibrahim Hussein | Kenya | 2:08:43 |
| 1989 | Abebe Mekonnen | Ethiopia | 2:09:06 |
| 1990 | Gelindo Bordin | Italy | 2:08:19 |
| 1991 | Ibrahim Hussein | Kenya | 2:11:06 |
| 1992 | Ibrahim Hussein | Kenya | 2:08:14 |
| 1993 | Cosmas Ndeti | Kenya | 2:09:33 |
| 1994 | Cosmas Ndeti | Kenya | 2:07:15 |
| 1995 | Cosmas Ndeti | Kenya | 2:09:22 |
| 1996 | Moses Tanui | Kenya | 2:09:15 |
| 1997 | Lameck Aguta | Kenya | 2:10:34 |
| 1998 | Moses Tanui | Kenya | 2:07:34 |
| 1999 | Joseph Chebet | Kenya | 2:09:52 |
| 2000 | Elijah Lagat | Kenya | 2:09:47 |
| 2001 | Lee Bong-Ju | South Korea | 2:09:43 |
| 2002 | Rodgers Rop | Kenya | 2:09:02 |
| 2003 | Robert Kipkoech Cheruiyot | Kenya | 2:10:11 |
| 2004 | Timothy Cherigat | Kenya | 2:10:37 |
| 2005 | Hailu Negussie | Ethiopia | 2:11:45 |
| 2006 | Robert Kipkoech Cheruiyot | Kenya | 2:07:14 |