| Derrick Milenkoff record | ||||
|---|---|---|---|---|
| Year | School | Won | Lost | Title |
| 2008 | Whiting | 0 | 21 | |
| 2009 | Whiting | 6 | 16 | |
| 2010 | Whiting | 2 | 19 | |
| 2011 | Whiting | 12 | 9 | |
| 2012 | Whiting | 13 | 8 | |
| 2013 | Whiting | 2 | 19 | |
| 2015 | River Forest | 14 | 9 | |
| 2016 | River Forest | 14 | 11 | |
| 2017 | River Forest | 18 | 6 | |
| 2018 | River Forest | 10 | 13 | |
| 2019 | River Forest | 9 | 14 | |
| 2020 | River Forest | 6 | 18 | |
| 2022 | Attica | 0 | 22 | |
| 2023 | Attica | 0 | 22 | |
| 2024 | Attica | 2 | 22 | |