| Plain Dealer Player of the Year | ||||
| Year | Player | School | Pos. | Grade |
| 1994 | Jason Levanduski | St. Edward | F | Sr. |
| 1995 | Ben Simon | Shaker Heights | F | Jr. |
| 1996 | Drew Carleton | University School | F | Sr. |
| 1997 | Anthony Balamenti | Trinity | F | Sr. |
| 1998 | Evan Schwartz | Shaker Heights | F | Sr. |
| 1999 | David Neundorfer | University School | F | Sr. |
| 2000 | Rashaun Ewing | Shaker Heights | F | Sr. |
| 2001 | Carson Strang | Shaker Heights | F | Sr. |
| 2002 | Patrick Neundorfer | University School | F | Sr. |
| 2003 | Kerry Cebul | University School | D | Sr. |
| 2004 | Elliot Taxman | University School | F | Sr. |
| 2005 | J.J. Plutt | Lake Catholic | F | Sr. |
| 2006 | Bill Fetsko | Lake Catholic | F | Sr. |
| 2007 | Gabe Taxman | University School | F | Sr. |
| 2008 | Richie Baker | Elyria Catholic | F | Sr. |
| 2009 | Pat Shedlock | University School | F | Sr. |
| 2010 | Sam Nader | St. Ignatius | D | Sr. |