| 1908 Walter Comstock, CHI 28:12 |
| 1909 H.B. Wasson, PUR 27:08 |
1910 E.J. Dohmen, WIS 26:21 (4.75 miles)
|
| 1911 C.R. Cleveland, WIS 29:43.2 |
| 1912 Irving White, WIS 27:29 |
| 1913 F.O. Watson, MINN 26:44.5 |
| 1914 F.O. Watson, MINN |
| 1915 F.O. Watson, MINN 26:14 |
| 1916 Glenn Tenny, CHI 26:25 |
| 1917-18: no Championship held |
| 1919 G.L. Otis, CHI |
| 1920 C.C. Furnas, PUR 26:30.6 |
| 1921 C.H. Finkle, WIS 29:12 |
| 1922 E.R. Isbell, MICH 26:33.2 |
| 1923 H.R. Phelps, IOWA 26:16 |
| 1924 H.R. Phelps, IOWA 25:59.7 |
| 1925 Vic Chapman, WIS 26:12 |
| 1926 Jock Hunn, IOWA 26:27.8 |
| 1927 John Zola, WIS 24:57 |
| 1928 David Abbott, ILL 26:42 |
| 1929 Orville Martin, PUR 26:26 |
| 1930 Rodney Leas, IND 26:27.7 |
| 1931 Henry Brocksmith, IND 21:59.7 |
| 1932 Dean Woolsey, IND 21:00.3 |
| 1933-37: no Championship held |
| 1938 Mel Trutt, IND 20:11.8 |
| 1939 Wally Mehl, WIS 20:34.7 |
| 1938 Mel Trutt, IND 20:11.8 |
| 1939 Wally Mehl, WIS 20:34.7 |
| 1940 Wayne Tolliver, IND 22:25.2 |
| 1941 Fred Wilt, IND 20:01.5 |
| 1942 Earl Mitchell, IND 21:09.2 |
| 1943 Eddie Ericsson, PUR 21:53.6 |
| 1944 William Lawson, WIS 21:16 |
| 1945 Victor Twomey, ILL 21:28.9 |
| 1946 Earl Mitchell, IND 21:10.8 |
| 1947 Don Gehrmann, WIS 20:26.4 |
| 1948 Don Gehrmann, WIS 20:31.4 |
| 1949 Don McEwen, MICH 19:44.5 |
| 1950 Don McEwen, MICH 19:34.3 |
| 1951 Walt Deike, WIS 21:12.3 |
| 1952 Rich Ferguson, IOWA 19:40.5 |
| 1953 Rich Ferguson, IOWA 19:43.2 |
| 1954 James Lambert, IND 19:59.6 |
| 1955 Henry Kennedy, MSU 19:06 |
| 1956 Henry Kennedy, MSU 20:25.3 |
| 1957 Leonard Edelen, MINN 21:09.4 |
| 1958 Charles Jones, IOWA 20:18 |
| 1959 Crawford Kennedy, MSU 20:12.3 |
| 1960 Gerald Young, MSU 19:35.3 |
| 1961 James Tucker, IOWA 19:50.4 |
| 1962 Allen Carius, ILL 19:45.2 |
| 1963 Allen Carius, ILL 19:39.4 |
| 1964 Lee Assenheimer, NU 20:11 |
| 1965 Lee Assenheimer, NU 20:05.2 |
| 1966 Larry Wierczorek, IOWA 19:02.5 |
|
| 1967 Larry Wierczorek, IOWA 24:17 |
| 1968 Doug Scorrar, OSU 24:49 |
| 1969 Garry Bjorklund, MINN 25:52.4 |
| 1970 Garry Bjorklund, MINN 24:33.7 |
| 1971 Garry Bjorklund, MINN 29:20.8 |
| 1972 Glenn Herold, WIS 29:46 |
| 1973 Craig Virgin, ILL 28:30.8 |
| 1974 Craig Virgin, ILL 29:11.4 |
| 1975 Craig Virgin, ILL 23:04.5 |
| 1976 Craig Virgin, ILL 23:16.7 |
| 1977 Bill Donakowski, MICH 24:14 |
| 1978 Steve Lacy, WIS 23:50 |
| 1980 Jim Spivey, IND 24:04.9 |
| 1981 Tim Hacker, WIS 24:05.3 |
| 1982 Jim Spivey, IND 24:20 |
| 1983 John Easker, WIS 23:22 |
| 1984 Tim Hacker, WIS 30:18.8 |
| 1985 Tim Hacker, WIS 24:27.4 |
| 1986 Chris Brewster, MICH 24:06.6 |
| 1987 Scott Williams, IND 24:31.11 |
| 1988 Bob Kennedy, IND 24:19 |
| 1989 Bob Kennedy, IND 24:03.8 |
| 1990 Bob Kennedy, IND 24:41.2 |
| 1991 Donovan Bergstrom, WIS 25:01.3 |
| 1992 Bob Kennedy, IND 23:31 |
| 1993 Kevin Sullivan, MICH 24:15.89 |
| 1994 Kevin Sullivan, MICH 24:15.4 |
| 1995 Kevin Sullivan, MICH 24:21.4 |
| 1996 John Mortimer, MICH 24:49.1 |
| 1997 Kevin Sullivan, MICH 23:42.7 |
| 1998 Matt Downin, WIS 24:06 |
| 1999 Matt Downin, WIS 24:57 |
| 2000 Jason Vanderhoof, WIS 24:01 |
| 2001 Alan Webb, MICH 23:19.9 |
| 2002 Matt Tegenkamp, WIS 24:01.9 |
| 2003 Simon Bairu, WIS 23:58.8 |
| 2004 Simon Bairu, WIS 23:45 |
| 2005 Simon Bairu, WIS 23:31.73 |
| 2006 Chris Rombough, MINN 24:05 |
| 2007 Matt Withrow, WIS 23:44.37 |
| 2008 |
| 2009 |
| 2010 |
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| 2012 |
| 2013 |
| 2014 |
| 2015 |
| 2012 |
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| 2014 |
| 2015 |
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