| Gary Cobb record | ||||
|---|---|---|---|---|
| Year | School | Won | Lost | Title |
| 2008 | New Haven | 5 | 15 | |
| 2009 | New Haven | 7 | 14 | |
| 2010 | New Haven | 10 | 11 | |
| 2011 | New Haven | 8 | 12 | |
| 2012 | New Haven | 6 | 15 | |
| 2014 | Woodlan | 14 | 7 | |
| 2015 | Woodlan | 7 | 16 | |
| 2016 | Woodlan | 13 | 11 | |
| 2017 | Woodlan | 12 | 12 | |
| 2018 | Woodlan | 8 | 15 | |
| 2019 | Woodlan | 15 | 8 | |
| 2020 | Woodlan | 18 | 7 | |
| 2021 | Woodlan | 9 | 13 | |
| 2022 | Woodlan | 19 | 5 | |
| 2023 | Woodlan | 20 | 5 | |