| Year | Sport | Individual | School | Event |
| 1978-79 | ||||
| 1979-80 | ||||
| 1980-81 | Track | Susan Neanen | National Trail | Long Jump |
| Track | Terri Thomas | Tri-Village | 800 M Run | |
| Track | Matt Vermillion | Tri-County North | Pole Vault | |
| 1981-82 | Track | Matt Vermillion | Tri-County North | Pole Vault |
| 1982-83 | Track | Chet Protzman | Tri-County North | Pole Vault |
| 1983-84 | Track | Kelly Deeter | Covington | 200 M Dash |
| 1984-85 | Track | Angie Clouse | Ansonia | Long Jump |
| 1985-86 | Girls’ Basketball | Bethel | ||
| Track | Rick Dunwoodie | Twin Valley South | High Jump | |
| 1986-87 | Track | Rick Dunwoodie | Twin Valley South | High Jump |
| 1987-88 | Track | Brad Mclean | Miami East | 3200 M Run |
| 1988-89 | ||||
| 1989-90 | Track | Terri Prescott | Ansonia | 800 M Run |
| Track | Josh Payne | Arcanum | 800 M Run | |
| Track | Josh Payne | Arcanum | 1600 M Run | |
| 1990-91 | ||||
| 1991-92 | Track | Heather Eubanks | National Trail | 1600 M Run |
| Track | David Haas | Tri-County North | 800 M Run | |
| 1992-93 | Track | Jason Unger | Miami East | Long Jump |
| Track | David Haas | Tri-County North | 800 M Run | |
| 1993-94 | ||||
| 1994-95 | Track | Jason Metzger | Twin Valley South | 800 M Run |
| 1995-96 | Boys’ Basketball | Miami East | ||
| 1996-97 | ||||
| 1997-98 | ||||
| 1998-99 | ||||
| 1999-2000 | Track | Luke Good | Twin Valley South | High Jump |
| 2000-01 | Boys’ Basketball | Bethel | ||
| 2001-02 | Track | Jeremy Ballard | National Trail | Discus |
| Track | Megan Makeski | Twin Valley South | Pole Vault | |
| 2002-03 | Track | Jon Sampson | Covington | Pole Vault |
| 2003-04 | ||||
| 2004-05 | Wrestling | Ryan Gambill | Miami East | 112 lb. |
| Cheerleading | Covington | OASSA Dance | ||
| 2005-06 | Wrestling | Logan Brown | Covington | 189 lb. |
| Track | Brooke Strayer | Arcanum | 300 M Hurdles | |
| 2006-07 | ||||
| Wrestling | Ryan Gambill | Miami East | 130 lb. | |
| 2007-08 | Wrestling | Ryan Gambill | Miami East | 135 lb. |
| Swimming | Lyndsey Farrel | Arcanum | 100 M Backstroke | |
| 2008-09 | Track | Kylie Kopp | Bethel | Long Jump |
| 2009-10 | Track | Juliane Accurso | Miami East | 1600 M Run |
| Softball | Newton | |||
| 2010-11 | ||||
| 2011-12 | Volleyball | Miami East | ||
| 2012-13 | Volleyball | Miami East | ||
| Track | Clayton Murphy | Tri-Village | 1600 M Run | |
| 2013-14 | Wrestling | Jarred Ganger | Covington | 126 lb. |
| Track | Jackie Siefring | Covington | Long Jump | |
| Track | Jackie Siefring | Covington | 300 M Hurdles | |
| Track | Lane White | Covington | 400 M Dash | |
| 2014-15 | Wrestling | Jarred Ganger | Covington | 132 lb. |
| Track | Aaron Deaton | Twin Valley South | Shot Put | |
| 2015-16 | Wrestling | Ben Sullivan | National Trail | 220 lb. |
| Boys’ Basketball | Tri-Village | |||
| Boys’ Bowling | Joe Teeter | Mississinawa Valley | ||
| Track | Aaron Deaton | Twin Valley South | Shot Put | |
| 2016-17 | Volleyball | Miami East | ||
| 2017-2018 | Wrestling | Graham Shore | Miami East | 120 lb. |
