Given annually to the player with the worst record at the end of the season, the “Bob Winterrose ‘Sey Tuff Guy’ Award” is one of the Coot Brown Golf League’s most coveted season-ending awards. The award honors the memory of long-time league member, Bob Winterrose.
| YEAR | GOLFER | RECORD |
| 2000 | Dave Hegger | 4-10-1 |
| 2001 | Al Keller | 2-8-1 |
| 2002 | Ray Gillick Sr. | 1-10-1 |
| 2003 | Bill Emling | 1-8-0 |
| 2004 | Matt Turek | 1-9-2 |
| 2005 | Paul Hillyard | 3-11-1 |
| 2006 | Norm Friedmeyer | 2-7-0 |
| 2007 | Greg Gillick | 3-12-1 |
| 2008 | Tom Heyl | 1-9-0 |
| 2009 | Chris Tockstein | 1-8-1 |
| 2010 | Tim Sargent | 3-9-1 |
| 2011 | Ed Williams | 2-10-2 |
| 2012 | Norm Friedmeyer | 2-6-0 |
| 2013 | Chris Caruso | 2-7-3 |
| 2014 | Paul Hillyard | 3-11-2 |
| 2015 | Kevin Oliver | 2-10-0 |
| 2016 | Juggie Hinduja | 0-7-0 |
| 2017 | Chris Caruso | 1-5-1 |
| 2018 | Doug Werner | 2-13-2 (.133) |
| 2019 | Herb Golterman | 2-7-0 (.222) |
| 2020 | Cory Newman | 1-4-3 (.200) |
| 2021 | Rob Gaylord | 1-7-0 (.125) |
| 2022 | Matt Gagnepain | 1-7-0 (.125) |
| 2023 | Chris Tockstein | 4-11-3 (.267) |
| 2024 | George Ermold | 0-12-2 (.000) |