| Year | Winning Team | Head Coach | Points | Runner-up | Head Coach | Points |
| 1928 | Lakewood | Bill Coccayne | 26 | Cincinnati Withrow | D.D. Gregg | 17 |
| 1929 | Lakewood | Bill Coccayne | 42 | Akron East | Larry Ricker | 11 |
| 1930 | Cincinnati Hughes | A.C. Kindschy | 21 | Lakewood | Russ Linden | 20 |
| 1931 | Cleveland YMCA Prep. | Larry Peterson | 27 | Canton McKinley | Ted Branin | 24 |
| 1932 | Cleleland Heights | Roy Uber | 19 | East Cleveland Shaw | Douglas Vivian | 15 |
| 1933 | Cleveland Heights | Roy Uber | 18 | Cincinnati Western Hills | Paul Nohr | 14.5 |
| 1934 | Cleveland Heights | Roy Uber | 34 | Shaker Heights | Harry Kyr | 12 |
| 1935 | Cincinnati Western Hills | Paul Nohr | 21 | Akron East | Larry Ricker | 14 |
| 1936 | Fremont Ross | N.B. Stults | 27 | Akron East | Larry Ricker | 18 |
| 1937 | Canton McKinley | Ted Branin | 31 | Fremont Ross | N.B. Stults | 24 |
| 1938 | Fremont Ross | N.B. Stults | 36 | Canton McKinley | Ted Branin | 27 |
| 1939 | Canton McKinley and Fremont Ross | Ted Branin and N.B. Stults | 39.5 | |||
| 1940 | Canton McKinley | Ted Branin | 42 | Fremont Ross | N.B. Stults | 34 |
| 1941 | Fremont Ross | N.B. Stults | 38 | Canton McKinley | Ted Branin | 25 |
| 1942 | Fremont Ross | N.B. Stults | 44 | Canton McKinley | Ted Branin | 25 |
| 1943 | Fremont Ross | John Titsworth | 36 | Lakewood | Russ Linden | 32 |
| 1944 | Findlay | Louis Keller & Roland Smith | 23 | Canton McKinley & Lakewood | Ted Branin & Jim Scullion | 17 |
| 1945 | Canton McKinley | Ted Branin | 31 | Cincinnati St. Xavier | 26 | |
| 1946 | Sandusky | Walter Caldwell | 25 | Canton Mckinley | Ted Branin | 23 |
| 1947 | Cleveland East Tech | Paul Scherer | 30 | Canton McKinley | Ted Branin | 26 |
| 1948 | Cleveland East Tech | Paul Scherer | 31 | Lakewood | Jim Scullion | 22 |
| 1949 | Canton McKinley | Ted Branin | 25 | Fremont Ross | George Gruse | 24 |
| 1950 | Cincinnati Walnut Hills | Whitey Davis | 34 | Fremont Ross | George Gruse | 27 |
| 1951 | Canton McKinley | Ted Branin | 52 | Cin. Walnut Hills | Whitey Davis | 30 |
| 1952 | Canton McKinley | Ted Branin | 46 | Fremont Ross | George Gruse | 29 |
| 1953 | Fremont Ross | George Gruse | 34 | Sandusky | Walter Caldwell | 29 |
| 1954 | Shaker Heights | Paul Stark | 42 | Cin. Walnut Hills and Lakewood | Whitey Davis and Jim Scullion | 33 |
| 1955 | Cincinnati Walnut Hills | Whitey Davis | 40 | Sandusky | Walter Caldwell | 33 |
| 1956 | Canton McKinley | Ted Branin | 46 | Sandusky | Walter Caldwell | 28 |
| 1957 | Canton McKinley | Ted Branin | 42 | Upper Arlington | Chester McPhee | 31 |
| 1958 | Canton McKinley | Ted Branin | 40 | Berea | David Thomas | 32 |
| 1959 | Canton McKinley | Ted Branin | 48 | Berea | David Thomas | 30 |
| 1960 | Canton McKinley | Ted Branin | 60 | Lakewood | Jim Scullion | 28 |
| 1961 | Canton McKinley | Ted Branin | 52 | Lima Senior | John Bruce | 35 |
| 1962 | Lakewood | Jim Scullion | 36 | Upper Arlington | R.W. Russell | 32 |
| 1963 | Akron Buchtel | Gordon Johnson | 41.5 | Cleveland Heights | Owen Johnson | 37 |
| 1964 | Fairview Park | Richard Segrist | 58 | Akron Buchtel | John McKay | 38.5 |
| 1965 | Cleveland Heights | Owen Johnson | 97 | Fairview Park | Richard Segrist | 95 |
| 1966 | Akron Firestone | R. Wells | 134 | Canton McKinley | Ted Branin | 92 |
| 1967 | Toledo St. Francis Desales | Ron Balatore | 171 | Akron Firestone | R.Wells | 141.5 |
| 1968 | Toledo St. Francis Desales | Ron Balatore | 152 | Upper Arlington | Todd Grant | 136.33 |
| 1969 | Akron Firestone | Dick Wells | 124 | Upper Arlington | Todd Grant | 117 |
| 1970 | Cincinnati St. Xavier | Dennis White | 159 | Upper Arlington | Todd Grant | 142 |
| 1971 | Cincinnati St. Xavier | Dennis White | 228 | Upper Arlington | Todd Grant | 123 |
| 1972 | Cincinnati St. Xavier | Dennis White | 252 | Upper Arlington | Todd Grant | 156 |
| 1973 | Cincinnati St. Xavier | Dennis White | 324 | Toledo St.Francis Desales | Butch Graves | 93 |
| 1974 | Cincinnati St. Xavier | Dennis White | 203 | Toledo St.Francis Desales | Butch Graves | 114 |
| 1975 | Cincinnati St. Xavier | Mike Arata | 181 | Upper Arlington | Todd Grant | 124 |
| 1976 | Cincinnati St. Xavier | Mike Arata | 159 | Upper Arlington | Todd Grant | 133 |
| 1977 | Cincinnati St. Xavier | Jim Loomis | 194 | Gates Mills Hawken | Jerry Holtrey | 160 |
| 1978 | Cincinnati St. Xavier | Jim Loomis | 215 | Upper Arlington | Todd Grant | 117 |
| 1979 | Cincinnati St. Xavier | Jim Loomis | 186 | Akron Firestone | Michael Wilcox | 142 |
| 1980 | Cincinnati St. Xavier | Dennis White | 178 | Akron Firestone | Michael Wilcox | 119 |
| 1981 | Cincinnati St. Xavier | Dennis White | 131 | Akron Firestone | Michael Wilcox | 118 |
| 1982 | Akron Firestone | Michael Wilcox | 155 | Cincinnati St. Xavier | Tim Blood | 116 |
| 1983 | Akron Firestone | Michael Wilcox | 166 | Cincinnati St. Xavier | Tim Blood | 160 |
| 1984 | Cincinnati St. Xavier | Mark Sullivan | 248 | Upper Arlington | Peter Linn | 115 |
| 1985 | Upper Arlington | Peter Linn | 162 | Cincinnati St. Xavier | Mark Sullivan | 150 |
| 1986 | Upper Arlington | Peter Linn | 190 | Cincinnati Sycamore | Larry Lyons | 113.5 |
| 1987 | Upper Arlington | Peter Linn | 159 | Gates Mills Hawken | Jerry Holtrey | 139 |
| 1988 | Gates Mills Hawken | Jerry Holtrey | 139.5 | North Canton Hoover | Richard Morrison | 104 |
| 1989 | Gates Mills Hawken | Jerry Holtrey | 132 | Akron Firestone | John Waldman | 95 |
| 1990 | Cincinnati St. Xavier | Jim Brower | 227 | Gates Mills Hawken | Jerry Holtrey | 110 |
| 1991 | Cincinnati St. Xavier | Jim Brower | 217 | Hudson | Kenwyn Chock | 141 |
| 1992 | Cincinnati St. Xavier | Jim Brower | 200.5 | Cleveland St. Ignatius | Mike Lehto | 145 |
| 1993 | Cincinnati St. Xavier | Jim Brower | 284 | Cleveland St. Ignatius | Mike Lehto | 220 |
| 1994 | Cincinnati St. Xavier | Jim Brower | 286 | Toledo St.Francis Desales | Ann Urschel | 209 |
| 1995 | Cincinnati St. Xavier | Jim Brower | 272.5 | Toledo St.Francis Desales | Ann Urschel | 263 |
| 1996 | Toledo St. Francis Desales | Ann Urschel | 253 | Cincinnati St. Xavier | David Coffman | 238 |
| 1997 | Cincinnati St. Xavier | David Coffman | 280 | Toledo St.Francis Desales | Chris Wolford | 271.5 |
| 1998 | Toledo St. Francis Desales | Chris Wolford | 307 | Cincinnati St. Xavier | David Coffman | 280 |
| 1999 | Cincinnati St. Xavier | David Coffman | 347 | Toledo St.Francis Desales | Chris Wolford | 278 |
| 2000 | Cincinnati St. Xavier | Jim Brower | 394 | Cleveland St. Ignatius | Rob Salisbury | 182 |
| 2001 | Cincinnati St. Xavier | Jim Brower | 333 | Centerville | Mark Davis | 171.5 |
| 2002 | Cincinnati St. Xavier | Jim Brower | 301 | Akron Firestone | Tim Lewarchick | 259 |
| 2003 | Cincinnati St. Xavier | Jim Brower | 316 | Upper Arlington | Kevin Chapman | 194 |
| 2004 | Cincinnati St. Xavier | Jim Brower | 263 | Upper Arlington | Kevin Chapman | 226 |
| 2005 | Cincinnati St. Xavier | Jim Brower | 259 | Upper Arlington | Kevin Chapman | 248.5 |
| 2006 | Cincnnati St. Xavier | Jim Brower | 289 | Columbus St. Charles | Kyle Goodwrich | 188 |