| SCHOOL YEAR | BOYS CROSS COUNTRY CONFERENCE CHAMPION |
| 1954-55 | |
| 1955-56 | |
| 1956-57 | |
| 1957-58 | |
| 1958-59 | |
| 1959-60 | |
| 1960-61 | |
| 1961-62 | Napoleon |
| 1962-63 | Napoleon |
| 1963-64 | East Jackson |
| 1964-65 | Napoleon |
| 1965-66 | Napoleon |
| 1966-67 | Napoleon |
| 1967-68 | East Jackson |
| 1968-69 | East Jackson |
| 1969-70 | East Jackson |
| 1970-71 | Vandercook Lake |
| 1971-72 | Northwest |
| 1972-73 | Northwest |
| 1973-74 | Northwest |
| 1974-75 | Northwest, Michigan Center |
| 1975-76 | Northwest |
| 1976-77 | Michigan Center |
| 1977-78 | East Jackson |
| 1978-79 | East Jackson |
| 1979-80 | East Jackson, Hanover-Horton |
| 1980-81 | Napoleon |
| 1981-82 | Napoleon |
| 1982-83 | Vandercook Lake |
| 1983-84 | Napoleon |
| 1984-85 | Napoleon |
| 1985-86 | Vandercook Lake |
| 1986-87 | Vandercook Lake |
| 1987-88 | Vandercook Lake |
| 1988-89 | Addison |
| 1989-90 | Addison, Napoleon |
| 1990-91 | Napoleon |
| 1991-92 | Michigan Center |
| 1992-93 | Napoleon |
| 1993-94 | Napoleon |
| 1994-95 | Grass Lake |
| 1995-96 | Grass Lake |
| 1996-97 | Grass Lake |
| 1997-98 | Grass Lake |
| 1998-99 | Grass Lake |
| 1999-00 | Grass Lake |
| 2000-01 | Addison |
| 2001-02 | Napoleon |
| 2002-03 | Vandercook Lake |
| 2003-04 | Vandercook Lake |
| 2004-05 | Addison |
| 2005-06 | Hanover-Horton, Vandercook Lake |
| 2006-07 | Hanover-Horton |
| 2007-08 | Hanover-Horton |
| 2008-09 | Hanover-Horton |
| 2009-10 | Hanover-Horton |
| 2010-11 | Napoleon |
| 2011-12 | Napoleon |
| 2012-13 | Napoleon |
| 2013-14 | Hanover-Horton |
| 2014-15 | Hanover-Horton |
| 2015-16 | Hanover-Horton |
| 2016-17 | Hanover-Horton |
| 2017-18 | Hanover-Horton |
| 2018-19 | Hanover-Horton |
| 2019-20 | Hanover-Horton |
| 2020-21 | Hanover-Horton |
| 2021-22 | Manchester |
| 2022-23 | Hanover-Horton |
Boys Cross Country league championships (1962-2022)
Addison (4): 1989, 1990t, 2001, 2005,
East Jackson (7): 1964, 1968, 1969, 1970, 1978, 1979, 1980t,
Grass Lake (6): 1995, 1996, 1997, 1998, 1999, 2000,
Hanover-Horton (15): 1980t, 2006t, 2007, 2008, 2009, 2010, 2013, 2014, 2015, 2016, 2017, 2018, 2019, 2020, 2022
Manchester (1); 2021
Michigan Center (3): 1975t, 1977, 1992,
Napoleon (17): 1962, 1963, 1965, 1966, 1967, 1981, 1982, 1984, 1985, 1990t, 1991, 1993, 1994, 2002, 2011, 2012, 2013
Northwest (5): 1972, 1973, 1974, 1975t, 1976,
Vandercook Lake (8): 1971, 1983, 1986, 1987, 1988, 2003, 2004, 2006t
CASCADES CONFERENCE 