Since 1995, WIN has honored the nation’s best wrestling writers and communicators who have promoted the sport with their work.
The following is a list of those Journalists of the Year.
| Year | Name, Organization |
| 2012 | Jeff Byers, Penn State Radio |
| 2011 | Andy Hamilton, Iowa City Press-Citizen |
| 2010 | Andrew Hipps, InterMat |
| 2009 | Jim Johnson, Big Ten Network and ESPN |
| 2008 | Kyle Klingman, On the Mat Radio |
| 2007 | Jason Bryant, InterMat |
| 2006 | Mike Chapman, WIN/Author |
| 2005 | Roger Moore, Stillwater (Okla.) NewsPress |
| 2004 | Craig Sesker, Omaha World Herald |
| 2003 | Rob Sherrill, WIN |
| 2002 | Gary Abbott, USA Wrestling |
| 2001 | Mike Nieto, Times of NW Indiana |
| 2000 | Dan Ventura, Boston Herald |
| 1999 | Jeff Byers, WRSC Radio |
| 1998 | Reid Handley, Chicago Tribune |
| 1997 | Dan McCool, Des Moines Register |
| 1996 | Matt Winkeljohn, Atlanta Journal-Constitution |
| 1995 | J.R. Ogden, Cedar Rapids Gazette |
