Cy Young
(2008 - Present)
| Season | Division | Player | Team | Stats |
| 2025 | North | Andy Neu | Kewaskum | 5-1, 3.10 ERA, 58 IP, 81 K's |
| South | Jack Ryan | Milton | 2-3, 2.63 ERA, 54.2 IP, 84 K's | |
| 2024 | North | Andy Neu | Kewaskum | 9-0, 1.12 ERA, 64 IP, 93 K's |
| South | Jack Ryan | Milton | 5-2, 3.43 ERA, 43.1 IP, 64 K's | |
| 2023 | North | Andy Neu | Kewaskum | 4-1, 3.50 ERA, 36 IP, 54 K's |
| South | Dan Dean | Milton | 4-1, 1.72 ERA, 57.2 IP, 52 K's | |
| 2022 | North | Grant Steinike | Cedarburg | 6-3, 2.84 ERA, 66.2 IP, 51 K's |
| South | Bayne Johnson | Neosho | 3-1, 2.68 ERA, 47 IP, 51 K's | |
| 2021 | North | Andrew Mueller | Hustisford | 5-3, 3.14 ERA, 66 IP, 64 K's |
| South | Brock Burg | Rubicon | 6-0, 1.20 ERA, 45 IP, 43 K's | |
| 2020 | North | None - COVID | ||
| South | None - COVID | |||
| 2019 | North | Sam Wilhelms | Brownsville | |
| South | Nick Klavekoske | Clyman | ||
| 2018 | North | Brody Marks | Hartford | |
| South | Brock Vredeveld | Clyman | ||
| 2017 | North | Jim Ziegler | Kewaskum | |
| South | Brad Wittnebel | Neosho | ||
| 2016 | North | David Rosser | Hustisford | |
| South | Brad Wittnebel | Neosho | ||
| South | Tyler Dierke | Madison Rockers | ||
| 2015 | North | Mitch Beau | Brownsville | |
| South | Shaun Panetti | Neosho | ||
| 2014 | North | Sam Wilhelms | Brownsville | |
| South | Sean McCann | Milton | ||
| 2013 | North | Sam Wilhelms | Brownsville | |
| South | Matt Sabel | Lebanon | ||
| 2012 | North | Sam Wilhelms | Brownsville | |
| South | Joe Shere | Milton | ||
| 2011 | North | Jim Ziegler | Kewaskum | |
| South | Joe Shere | Milton | ||
| 2010 | North | Chris Rowoldt | Rubicon | |
| South | Joe Shere | Milton | ||
| 2009 | North | Chris Rowoldt | Rubicon | |
| South | Jeff Zielke | Clyman | ||
| 2008 | North | Chris Morgan | Oakfield | |
| South | Jeff Zielke | Clyman | ||
