| Middletown | Monroe-Woodbury | Newburgh FA | Pine Bush | |||||||||||||||||||||||||
| 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 | 8 | 10 | 9 | 2000 | 19 | 3 | A | 9 | Sect 9 A Semis | 2000 | 12 | 9 | A | 9 | 2000 | 17 | 6 | A | 9 | Sect 9 A Champ | ||||||||
| 2001 | 17 | 7 | A | 9 | Sect 9 A Champ | 2001 | 14 | 7 | A | 9 | 2001 | 13 | 10 | A | 9 | Sect 9 A 2nd | 2001 | 5 | 15 | 9 | ||||||||
| 2002 | 8 | 12 | 9 | 2002 | 16 | 6 | A | 9 | Sect 9 A 2nd | 2002 | 12 | 10 | A | 9 | Sect 9 A Semis | 2002 | 3 | 17 | 9 | |||||||||
| 2003 | 6 | 14 | 9 | 2003 | 9 | 11 | 9 | 2003 | 16 | 4 | A | 9 | Sect 9 A Semis | 2003 | 2 | 17 | 9 | |||||||||||
| 2004 | 15 | 7 | AA | 9 | Sect 9 AA Semis | 2004 | 14 | 7 | AA | 9 | 2004 | 19 | 4 | AA | 9 | Sect 9 AA 2nd | 2004 | 5 | 15 | 9 | ||||||||
| 2005 | 14 | 7 | AA | 9 | 2005 | 16 | 8 | AA | 9 | Sect 9 AA Champ | 2005 | 18 | 4 | AA | 9 | Sect 9 AA Semis | 2005 | 12 | 9 | AA | 9 | |||||||
| 2006 | 5 | 15 | 9 | 2006 | 16 | 7 | AA | 9 | Sect 9 AA 2nd | 2006 | 20 | 3 | AA | 9 | Sect 9 AA Champ | 2006 | 5 | 15 | 9 | |||||||||
| 2007 | 9 | 12 | AA | 9 | 2007 | 8 | 12 | 9 | 2007 | 21 | 2 | AA | 9 | Sect 9 AA Champ | 2007 | 4 | 16 | 9 | ||||||||||
| 2008 | 14 | 7 | AA | 9 | Sect 9 AA Semis | 2008 | 13 | 7 | AA | 9 | 2008 | 17 | 6 | AA | 9 | Sect 9 AA 2nd | 2008 | 1 | 19 | 9 | ||||||||
| 2009 | 3 | 16 | 9 | 2009 | 14 | 6 | AA | 9 | Sect 9 AA Semis | 2009 | 20 | 5 | AA | 9 | Federation AA 2nd | 2009 | 11 | 10 | AA | 9 | ||||||||
| 2010 | 17 | 3 | AA | 9 | Sectin 9 AA 2nd | 2010 | 10 | 9 | AA | 9 | 2010 | 18 | 3 | AA | 9 | State AA Semis | 2010 | 2 | 16 | 9 | ||||||||
| 2011 | 14 | 7 | AA | 9 | Sect 9 AA 2nd | 2011 | 5 | 13 | 9 | 2011 | 17 | 5 | AA | 9 | Sect 9 AA Champ | 2011 | 5 | 13 | 9 | |||||||||
| 2012 | 15 | 8 | AA | 9 | Sect 9 AA Champ | 2012 | 3 | 15 | 9 | 2012 | 14 | 5 | AA | 9 | Sect 9 AA Semis | 2012 | 5 | 13 | 9 | |||||||||
| 2013 | 12 | 8 | AA | 9 | Sect 9 AA Semis | 2013 | 6 | 12 | 9 | 2013 | 12 | 6 | AA | 9 | Sect 9 AA Semis | 2013 | 2 | 16 | 9 | |||||||||
| 2014 | 12 | 7 | AA | 9 | Sect 9 AA Semis | 2014 | 4 | 14 | 9 | 2014 | 20 | 2 | AA | 9 | Sect 9 AA Champ | 2014 | 6 | 12 | 9 | |||||||||
| 2015 | 20 | 3 | AA | 9 | Sect 9 AA Champ | 2015 | 10 | 9 | AA | 9 | 2015 | 8 | 11 | AA | 9 | 2015 | 11 | 9 | AA | 9 | Sect 9 AA Semis | |||||||
| 2016 | 20 | 5 | AA | 9 | State AA Semis | 2016 | 7 | 13 | 9 | 2016 | 8 | 12 | 9 | 2016 | 18 | 2 | AA | 9 | Sect 9 AA Semis | |||||||||
| 2017 | 6 | 13 | AA | 9 | 2017 | 11 | 10 | AA | 9 | 2017 | 11 | 9 | AA | 9 | 2017 | 21 | 1 | AA | 9 | Sect 9 AA Champ | ||||||||
| 2018 | 15 | 7 | AA | 9 | Sect 9 AA Semis | 2018 | 10 | 11 | AA | 9 | 2018 | 11 | 11 | AA | 9 | 2018 | 23 | 2 | AA | 9 | Sect 9 AA Champ | |||||||
| 2019 | 16 | 6 | AA | 9 | Sect 9 AA 2nd | 2019 | 7 | 13 | 9 | 2019 | 11 | 9 | AA | 9 | Sect 9 AA Semis | 2019 | 6 | 14 | 9 | |||||||||
| 2020 | 7 | 13 | 9 | 2020 | 9 | 11 | 9 | 2020 | 20 | 3 | AA | 9 | Sect 9 AA Champ | 2020 | 15 | 7 | AA | 9 | Sect 9 AA 2nd | |||||||||
| 2021 | 3 | 2 | 9 | 2021 | x | x | x | 9 | 2021 | x | x | x | 9 | 2021 | 5 | 3 | 9 | |||||||||||
| 2022 | 14 | 8 | AA | 9 | Sect 9 AA 2nd | 2022 | 12 | 9 | AA | 9 | 2022 | 16 | 4 | AA | 9 | Sect 9 AA Champ | 2022 | 11 | 10 | AA | 9 | Sect 9 AA Semis | ||||||
| 2023 | 12 | 10 | AA | 9 | Sect 9 AA 2nd | 2023 | 12 | 9 | AA | 9 | 2023 | 14 | 8 | AA | 9 | Sect 9 AA Champ | 2023 | 0 | 20 | 9 | ||||||||
| 2024 | 6 | 14 | 9 | 2024 | 16 | 6 | AAA | 9 | Sect 9 AAA 2nd | 2024 | 9 | 12 | AA | 9 | Sect 9 AAA Semis | 2024 | 6 | 13 | 9 | |||||||||
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