| Year | Div | Winner | Head Coach | Pts | Tie? | Runner Up | Head Coach | Pts |
| 1928 | 1 | Lakewood | Bill Coccayne | 26 | Cincinnati Withrow | D.D. Gregg | 17 | |
| 1929 | 1 | Lakewood | Bill Coccayne | 42 | Akron East | Larry Ricker | 11 | |
| 1930 | 1 | Cincinnati Hughes | A.C. Kindschy | 21 | Lakewood | Russ Linden | 20 | |
| 1931 | 1 | Cleveland YMCA Prep. | Larry Peterson | 27 | Canton McKinley | Ted Branin | 24 | |
| 1932 | 1 | Cleveland Heights | Roy Uber | 19 | East Cleveland Shaw | Douglas Vivian | 15 | |
| 1933 | 1 | Cleveland Heights | Roy Uber | 18 | Cincinnati Western Hills | Paul Nohr | 14.5 | |
| 1934 | 1 | Cleveland Heights | Roy Uber | 34 | Shaker Heights | Harry Kyr | 12 | |
| 1935 | 1 | Cincinnati Western Hills | Paul Nohr | 21 | Akron East | Larry Ricker | 14 | |
| 1936 | 1 | Fremont Ross | N.B. Stults | 27 | Akron East | Larry Ricker | 18 | |
| 1937 | 1 | Canton McKinley | Ted Branin | 31 | Fremont Ross | N.B. Stults | 24 | |
| 1938 | 1 | Fremont Ross | N.B. Stults | 36 | Canton McKinley | Ted Branin | 27 | |
| 1939 | 1 | Canton McKinley | Ted Branin | 39.5 | Tie | Fremont Ross | G.M. Gruse | 39.5 |
| 1940 | 1 | Canton McKinley | Ted Branin | 42 | Fremont Ross | N.B. Stults | 34 | |
| 1941 | 1 | Fremont Ross | N.B. Stults | 38 | Canton McKinley | Ted Branin | 25 | |
| 1942 | 1 | Fremont Ross | N.B. Stults | 44 | Canton McKinley | Ted Branin | 25 | |
| 1943 | 1 | Fremont Ross | J. Titsworth | 36 | Lakewood | Russ Linden | 32 | |
| 1944 | 1 | Findlay | Louis Keller & Roland Smith | 23 | Canton McKinley | Ted Branin | 17 | |
| 1944 | 1 | Lakewood | Jim Scullion | 17 | ||||
| 1945 | 1 | Canton McKinley | Ted Branin | 31 | Cincinnati St. Xavier | unknown | 26 | |
| 1946 | 1 | Sandusky | Walter Caldwell | 25 | Canton McKinley | Ted Branin | 23 | |
| 1947 | 1 | Cleveland East Tech | Paul Scherer | 30 | Canton McKinley | Ted Branin | 26 | |
| 1948 | 1 | Cleveland East Tech | Paul Scherer | 31 | Lakewood | Jim Scullion | 22 | |
| 1949 | 1 | Canton McKinley | Ted Branin | 25 | Fremont Ross | G.M . Gruse | 24 | |
| 1950 | 1 | Cincinnati Walnut Hills | Whitey Davis | 34 | Fremont Ross | G.M . Gruse | 27 | |
| 1951 | 1 | Canton McKinley | Ted Branin | 52 | Cincinnati Walnut Hills | Whitey Davis | 30 | |
| 1952 | 1 | Canton McKinley | Ted Branin | 46 | Fremont Ross | G.M. Gruse | 29 | |
| 1953 | 1 | Fremont Ross | G.M . Gruse | 34 | Sandusky | Walter Caldwell | 29 | |
| 1954 | 1 | Shaker Heights | Paul Stark | 42 | Cincinnati Walnut Hills | Whitey Davis | 33 | |
| 1954 | 1 | Lakewood | Jim Scullion | 33 | ||||
| 1955 | 1 | Cincinnati Walnut Hills | Whitey Davis | 40 | Sandusky | Walter Caldwell | 33 | |
| 1956 | 1 | Canton McKinley | Ted Branin | 46 | Sandusky | Walter Caldwell | 28 | |
| 1957 | 1 | Canton McKinley | Ted Branin | 42 | Upper Arlington | Chester McPhee | 31 | |
| 1958 | 1 | Canton McKinley | Ted Branin | 40 | Berea | David Thomas | 32 | |
| 1959 | 1 | Canton McKinley | Ted Branin | 48 | Berea | David Thomas | 30 | |
| 1960 | 1 | Canton McKinley | Ted Branin | 60 | Lakewood | Jim Scullion | 28 | |
| 1961 | 1 | Canton McKinley | Ted Branin | 52 | Lima Senior | John Bruce | 35 | |
| 1962 | 1 | Lakewood | Jim Scullion | 36 | Upper Arlington | R.W. Russell | 32 | |
| 1963 | 1 | Akron Buchtel | Gordon Johnson | 41.5 | Cleveland Heights | Owen Johnson | 37 | |
| 1964 | 1 | Fairview Park | Richard Segrist | 58 | Akron Buchtel | John McKay | 38.5 | |
| 1965 | 1 | Cleveland Heights | Owen Johnson | 97 | Fairview Park Fairview | Richard Segrist | 95 | |
| 1966 | 1 | Akron Firestone | Dick Wells | 134 | Canton McKinley | Ted Branin | 92 | |
| 1967 | 1 | Toledo St. Francis deSales | Ron Balatore | 171 | Akron Firestone | R. Wells | 141.5 | |
| 1968 | 1 | Toledo St. Francis deSales | Ron Balatore | 152 | Upper Arlington | Todd Grant | 136.33 | |
| 1969 | 1 | Akron Firestone | Dick Wells | 124 | Upper Arlington | Todd Grant | 117 | |
| 1970 | 1 | Cincinnati St. Xavier | Dennis White | 159 | Upper Arlington | Todd Grant | 142 | |
| 1971 | 1 | Cincinnati St. Xavier | Dennis White | 228 | Upper Arlington | Todd Grant | 123 | |
| 1972 | 1 | Cincinnati St. Xavier | Dennis White | 252 | Upper Arlington | Todd Grant | 156 | |
| 1973 | 1 | Cincinnati St. Xavier | Dennis White | 324 | Toledo St. Francis deSales | Dennis Graves | 93 | |
| 1974 | 1 | Cincinnati St. Xavier | Mike Arata | 203 | Toledo St. Francis deSales | Dennis Graves | 114 | |
| 1975 | 1 | Cincinnati St. Xavier | Mike Arata | 181 | Upper Arlington | Todd Grant | 124 | |
| 1976 | 1 | Cincinnati St. Xavier | Mike Arata | 159 | Upper Arlington | Todd Grant | 133 | |
| 1977 | 1 | Cincinnati St. Xavier | Jim Loomis | 194 | Gates Mills Hawken | Jerry Holtrey | 160 | |
| 1978 | 1 | Cincinnati St. Xavier | Jim Loomis | 215 | Upper Arlington | Todd Grant | 117 | |
| 1979 | 1 | Cincinnati St. Xavier | Jim Loomis | 186 | Akron Firestone | Michael Wilcox | 142 | |
| 1980 | 1 | Cincinnati St. Xavier | Dennis White | 178 | Akron Firestone | Michael Wilcox | 119 | |
| 1981 | 1 | Cincinnati St. Xavier | Dennis White | 131 | Akron Firestone | Michael Wilcox | 118 | |
| 1982 | 1 | Akron Firestone | Michael Wilcox | 155 | Cincinnati St. Xavier | Tim Blood | 116 | |
| 1983 | 1 | Akron Firestone | Michael Wilcox | 166 | Cincinnati St. Xavier | Tim Blood | 160 | |
| 1984 | 1 | Cincinnati St. Xavier | Mark Sullivan | 248 | Upper Arlington | Peter Linn | 115 | |
| 1985 | 1 | Upper Arlington | Peter Linn | 162 | Cincinnati St. Xavier | Mark Sullivan | 150 | |
| 1986 | 1 | Upper Arlington | Peter Linn | 190 | Cincinnati Sycamore | Larry Lyons | 113.5 | |
| 1987 | 1 | Upper Arlington | Peter Linn | 159 | Gates Mills Hawken | Jerry Holtrey | 139 | |
| 1988 | 1 | Gates Mills Hawken | Jerry Holtrey | 139.5 | North Canton Hoover | Richard Morrison | 104 | |
| 1989 | 1 | Gates Mills Hawken | Jerry Holtrey | 132 | Akron Firestone | Eric Smith | 95 | |
| 1990 | 1 | Cincinnati St. Xavier | Jim Brower | 227 | Gates Mills Hawken | Jerry Holtrey | 110 | |
| 1991 | 1 | Cincinnati St. Xavier | Jim Brower | 217 | Hudson | Kenwyn Chock | 141 | |
| 1992 | 1 | Cincinnati St. Xavier | Jim Brower | 200.5 | Cleveland St. Ignatius | Mike Lehto | 145 | |
| 1993 | 1 | Cincinnati St. Xavier | Jim Brower | 284 | Cleveland St. Ignatius | Mike Lehto | 220 | |
| 1994 | 1 | Cincinnati St. Xavier | Jim Brower | 286 | Toledo St. Francis deSales | Ann Urschel | 209 | |
| 1995 | 1 | Cincinnati St. Xavier | David Coffman | 272.5 | Toledo St. Francis deSales | Ann Urschel | 263 | |
| 1996 | 1 | Toledo St. Francis deSales | Ann Urschel | 253 | Cincinnati St. Xavier | David Coffman | 238 | |
| 1997 | 1 | Cincinnati St. Xavier | David Coffman | 280 | Toledo St. Francis deSales | Chris Wolford | 271.5 | |
| 1998 | 1 | Toledo St. Francis deSales | Chris Wolford | 307 | Cincinnati St. Xavier | David Coffman | 280 | |
| 1999 | 1 | Cincinnati St. Xavier | Jim Brower | 347 | Toledo St. Francis deSales | Chris Wolford | 278 | |
| 2000 | 1 | Cincinnati St. Xavier | Jim Brower | 394 | Cleveland St. Ignatius | Rob Salisbury | 182 | |
| 2001 | 1 | Cincinnati St. Xavier | Jim Brower | 333 | Centerville | Mark Davis | 171.5 | |
| 2002 | 1 | Cincinnati St. Xavier | Jim Brower | 301 | Akron Firestone | Tim Lewarchick | 259 | |
| 2003 | 1 | Cincinnati St. Xavier | Jim Brower | 316 | Upper Arlington | Kevin Chapman | 194 | |
| 2004 | 1 | Cincinnati St. Xavier | Jim Brower | 263 | Upper Arlington | Kevin Chapman | 226 | |
| 2005 | 1 | Cincinnati St. Xavier | Jim Brower | 259 | Upper Arlington | Kevin Chapman/Kelly King | 248.5 | |
| 2006 | 1 | Cincinnati St. Xavier | Jim Brower | 289 | Columbus St. Charles | Kyle Goodrich | 188 | |
| 2007 | 1 | Cincinnati St. Xavier | Jim Brower | 250 | Columbus St. Charles | Kyle Goodrich | 177 | |
| 2008 | 1 | Columbus St. Charles | Kyle Goodrich | 266 | Cincinnati St. Xavier | Jim Brower | 246 | |
| 2009 | 1 | Cincinnati St. Xavier | Jim Brower | 322 | Columbus St. Charles | Kyle Goodrich | 265 | |
| 2009 | 2 | Hunting Valley University School | Brian Perry | 288 | Cincinnati Wyoming | David Elliott | 180 | |
| 2010 | 1 | Cincinnati St. Xavier | Jim Brower | 228 | Toledo St. Francis deSales | Keith Kennedy | 218 | |
| 2010 | 2 | Hunting Valley University School | Brian Perry | 298 | Cincinnati Wyoming | David Elliott | 250 | |
| 2011 | 1 | Cincinnati St. Xavier | Jim Brower | 312 | Toledo St. Francis deSales | Keith Kennedy | 298.5 | |
| 2011 | 2 | Hunting Valley University School | Brian Perry | 377 | Cincinnati Wyoming | David Elliott | 191 | |
| 2012 | 1 | Cincinnati St. Xavier | Jim Brower | 297.5 | Upper Arlington | Mike DeBear | 198 | |
| 2012 | 2 | Hunting Valley University School | Brian Perry | 237.5 | Dayton Oakwood | Jen Jervis | 231 | |
| 2013 | 1 | Cincinnati St. Xavier | Jim Brower | 270 | Upper Arlington | Mike DeBear | 187.5 | |
| 2013 | 2 | Dayton Oakwood | Jen Jervis | 288 | Hunting Valley University School | Brian Perry | 169 | |
| 2014 | 1 | Cincinnati St. Xavier | Jim Brower | 255 | Toledo St. Francis deSales | Brent Ransom | 238 | |
| 2014 | 2 | Dayton Oakwood | Jen Jervis | 214 | Gates Mills Hawken | Jerry Holtrey | 185 | |
| 2015 | 1 | Cincinnati St. Xavier | Jim Brower | 335 | Cincinnati Archbishop Moeller | William Whatley | 134 | |
| 2015 | 2 | Cincinnati Seven Hills | Allie Henges | 209 | Dover | Brenda Wherley | 152 | |
| 2016 | 1 | Cincinnati St. Xavier | Tim Beerman | 398 | Brecksville Broadview Heights | Mark Krusinski | 179 | |
| 2016 | 2 | Cincinnati Seven Hills | Allie Henges | 267 | Gates Mills Hawken | Jim Bocci | 188 | |
| 2017 | 1 | Cincinnati St. Xavier | Tim Beerman | 434 | Cleveland St. Ignatius | Mike Lehto | 173 | |
| 2017 | 2 | Gates Mills Hawken | Todd Clark | 230 | Cincinnati Seven Hills | Brandon Williams | 171 | |
| 2018 | 1 | Cincinnati St. Xavier | Tim Beerman | 413 | Brecksville-Broadview Heights | Mark Krusinski | 150 | |
| 2018 | 2 | Hunting Valley University School | Brian Perry | 219.5 | Gates Mills Hawken | Todd Clark | 211.5 | |
| 2019 | 1 | Cincinnati St. Xavier | Tim Beerman | 310 | Sycamore | Dan Carl | 240 | |
| 2019 | 2 | Hunting Valley University School | Brian Perry | 331 | Gates Mills Hawken | Todd Clark | 212 | |
| 2020 | 1 | Cincinnati St. Xavier | Tim Beerman | 310 | Upper Arlington | Mike de Bear | 201 | |
| 2020 | 2 | Cincinnati Indian Hill | Matt Harrison | 224 | Hunting Valley University School | Brian Perry | 216 | |
| 2021 | 1 | Cincinnati St. Xavier | Dave Albert | 261.5 | Upper Arlington | Mike de Bear | 190 | |
| 2021 | 2 | Gates Mills Hawken | Tim Hable | 228 | Cincinnati Indian Hill | Matt Harrison | 145 | |
| 2022 | 1 | Beavercreek | Chris Meleason | 211.5 | Cincinnati St. Xavier | Dave Albert | 207.5 | |
| 2022 | 2 | Hunting Valley University School | Brian Perry | 188 | Rocky River | Mark Harris | 156 | |
| 2023 | 1 | Cincinnati St. Xavier | Dave Albert | 287 | Upper Arlington | Mike de Bear | 182 | |
| 2023 | 2 | Hunting Valley University School | Brian Perry | 290.5 | Indian Hill | Matt Harrison | 172 |