| Plain Dealer Coach of the Year | ||
| Year | Coach | School |
| 1994 | Bob Whidden | St. Edward |
| 1995 | Doug Hauser | Padua |
| 1996 | Doug Hauser | Padua |
| 1997 | John Malloy | Rocky River |
| 1998 | Bob Whidden | St. Edward |
| 1999 | Bill Beard | University School |
| 2000 | Dick Homovec | Euclid |
| 2001 | Mike Bartley | Shaker Heights |
| 2002 | Bob Whidden | St. Edward |
| 2003 | Bill Beard | University School |
| 2004 | Bob Whidden | St. Edward |
| 2005 | Bob Whidden | St. Edward |
| 2006 | Tony Prpic | Lake Catholic |
| 2007 | Dave Phiel | Elyria Catholic |
| 2008 | Rob Whidden | St. Edward |
| 2009 | Bill Beard | University School |
| 2010 | Patrick O'Rourke | St. Ignatius |