| Millbrook | Pawling | Pine Plains | Webutuck | |||||||||||||||||||||||||
| Year | W | L | CL | S | Accomp | Year | W | L | CL | S | Accomp | Year | W | L | CL | S | Accomp | Year | W | L | CL | S | Accomp | |||||
| 2000 | 13 | 8 | C | 9 | Sect 9 C 2nd | 2000 | 0 | 21 | 1 | 2000 | 12 | 10 | C | 9 | Sect 9 C Semis | 2000 | 1 | 17 | 9 | |||||||||
| 2001 | 13 | 8 | C | 9 | Sect 9 C 2nd | 2001 | No Team in 2001 | 2001 | 7 | 14 | C | 9 | Sect 9 C Semis | 2001 | 0 | 16 | 9 | |||||||||||
| 2002 | 14 | 8 | C | 9 | Sect 9 C 2nd | 2002 | 12 | 9 | C | 1 | 2002 | 11 | 10 | C | 9 | 2002 | 2 | 15 | 9 | |||||||||
| 2003 | 13 | 7 | C | 9 | Sect 9 C Semis | 2003 | 10 | 11 | C | 1 | 2003 | 8 | 12 | 9 | 2003 | 2 | 18 | 9 | ||||||||||
| 2004 | 18 | 5 | C | 9 | Sect 9 C Champ | 2004 | 6 | 14 | 1 | 2004 | 11 | 10 | C | 9 | 2004 | 5 | 15 | 9 | ||||||||||
| 2005 | 17 | 5 | C | 9 | Sect 9 C Champ | 2005 | 4 | 14 | 1 | 2005 | 15 | 7 | C | 9 | Sect 9 C 2nd | 2005 | 14 | 8 | C | 9 | Sect 9 C Semis | |||||||
| 2006 | 18 | 6 | C | 9 | Sect 9 C Champ | 2006 | 5 | 15 | 1 | 2006 | 16 | 5 | B | 9 | Sect 9 B Semis | 2006 | 12 | 10 | C | 9 | Sect 9 C Semis | |||||||
| 2007 | 15 | 6 | C | 9 | Sect 9 C 2nd | 2007 | 4 | 16 | 1 | 2007 | 12 | 9 | B | 9 | 2007 | 14 | 7 | C | 9 | Sect 9 C Semis | ||||||||
| 2008 | 15 | 10 | C | 9 | Sect 9 C Champ | 2008 | 8 | 11 | B | 1 | 2008 | 5 | 15 | B | 9 | 2008 | 14 | 6 | C | 9 | Sect 9 C Semis | |||||||
| 2009 | 14 | 8 | C | 9 | Sect 9 C Champ | 2009 | 18 | 3 | B | 1 | 2009 | 11 | 9 | C | 9 | 2009 | 3 | 17 | 9 | |||||||||
| 2010 | 9 | 11 | C | 9 | Sect 9 C Semis | 2010 | 3 | 16 | 1 | 2010 | 10 | 9 | C | 9 | 2010 | 0 | 18 | 9 | ||||||||||
| 2011 | 12 | 6 | C | 9 | Sect 9 C Semis | 2011 | 3 | 15 | 1 | 2011 | 17 | 5 | C | 9 | Sect 9 C Champ | 2011 | 0 | 18 | 9 | |||||||||
| 2012 | 14 | 9 | C | 9 | Sect 9 C 2nd | 2012 | 12 | 8 | B | 1 | 2012 | 19 | 3 | C | 9 | Sect 9 C Champ | 2012 | 0 | 18 | 9 | ||||||||
| 2013 | 7 | 10 | C | 9 | 2013 | 11 | 8 | B | 1 | 2013 | 21 | 3 | C | 9 | State C 2nd | 2013 | 1 | 17 | 9 | |||||||||
| 2014 | 12 | 8 | B | 9 | Sect 9 B Semis | 2014 | 6 | 11 | 1 | 2014 | 1 | 17 | 9 | 2014 | 4 | 15 | C | 9 | Sect 9 C Semis | |||||||||
| 2015 | 7 | 11 | B | 9 | 2015 | 3 | 15 | 1 | 2015 | 1 | 17 | 9 | 2015 | 5 | 12 | 9 | ||||||||||||
| 2016 | 5 | 13 | C | 9 | 2016 | 6 | 14 | 1 | 2016 | 3 | 13 | 9 | 2016 | 8 | 13 | C | 9 | |||||||||||
| 2017 | 16 | 7 | C | 9 | Sect 9 C Champ | 2017 | 7 | 14 | C | 1 | 2017 | 10 | 11 | C | 9 | 2017 | 6 | 15 | C | 9 | ||||||||
| 2018 | 18 | 5 | C | 9 | Sect 9 C Champ | 2018 | 7 | 14 | C | 1 | 2018 | 10 | 9 | C | 9 | 2018 | 2 | 17 | D | 9 | ||||||||
| 2019 | 16 | 6 | C | 9 | Sect 9 C Champ | 2019 | 8 | 13 | B | 1 | 2019 | 12 | 10 | C | 9 | 2019 | 2 | 15 | 9 | |||||||||
| 2020 | 12 | 10 | C | 9 | 2020 | 10 | 12 | B | 1 | 2020 | 13 | 10 | C | 9 | Sect 9 C Champ | 2020 | 0 | 18 | 9 | |||||||||
| 2021 | 4 | 4 | 9 | 2021 | 0 | 3 | B | 1 | 2021 | 3 | 4 | 9 | 2021 | 0 | 6 | 9 | ||||||||||||
| 2022 | 8 | 10 | C | 9 | 2022 | 4 | 18 | B | 1 | 2022 | 11 | 5 | C | 9 | Sect 9 C 2nd | 2022 | 0 | 16 | 9 | |||||||||
| 2023 | 8 | 11 | C | 9 | Sect 9 C Semis | 2023 | 3 | 17 | 1 | 2023 | 9 | 9 | C | 9 | Sect 9 C 2nd | 2023 | 1 | 17 | 9 | |||||||||
| 2024 | 12 | 7 | C | 9 | Sect 9 C Champs | 2024 | 4 | 15 | 1 | 2024 | 5 | 12 | C | 9 | Sect 9 C Semis | 2024 | 0 | 20 | 9 | |||||||||
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