| Derrick Milenkoff record | |||||
|---|---|---|---|---|---|
| Year | School | Won | Lost | Title | Class |
| 2007-08 | Whiting | 0 | 21 | 1A | |
| 2008-09 | Whiting | 6 | 16 | 1A | |
| 2009-10 | Whiting | 2 | 19 | 1A | |
| 2010-11 | Whiting | 12 | 9 | 1A | |
| 2011-12 | Whiting | 13 | 8 | 2A | |
| 2012-13 | Whiting | 2 | 19 | 2A | |
| 2014-15 | River Forest | 14 | 9 | 2A | |
| 2015-16 | River Forest | 14 | 11 | 2A | |
| 2016-17 | River Forest | 18 | 6 | 2A | |
| 2017-18 | River Forest | 10 | 13 | 2A | |
| 2018-19 | River Forest | 9 | 14 | 2A | |
| 2019-20 | River Forest | 6 | 18 | 3A | |
| 2021-22 | Attica | 0 | 22 | 1A | |
| 2022-23 | Attica | 0 | 22 | 1A | |
| 2023-24 | Attica | 2 | 22 | 1A | |