| Ryan Haywood record | ||||
|---|---|---|---|---|
| Year | School | Won | Lost | Title |
| 2006 | Mount Carmel (Ill.) | 0 | 0 | |
| 2007 | Mount Carmel (Ill.) | 0 | 0 | |
| 2008 | Mount Carmel (Ill.) | 0 | 0 | |
| 2009 | Mount Carmel (Ill.) | 0 | 0 | |
| 2010 | Mount Carmel (Ill.) | 0 | 0 | |
| 2011 | Mount Carmel (Ill.) | 0 | 0 | |
| 2012 | Princeton | 10 | 14 | |
| 2013 | Princeton | 10 | 13 | |
| 2014 | Princeton | 17 | 7 | |
| 2015 | Princeton | 2 | 21 | |
| 2016 | Princeton | 2 | 23 | |
| 2017 | Princeton | 10 | 14 | |
| 2018 | Princeton | 19 | 5 | |
| 2019 | Princeton | 21 | 6 | sectional |
| 2020 | Loogootee | 18 | 6 | |
| 2021 | Loogootee | 20 | 4 | |
| 2022 | Loogootee | 18 | 6 | |
| 2023 | Loogootee | 20 | 8 | regional |
| 2024 | Southridge | 19 | 7 | sectional |