| Section 9 Champions | ||||||||
| HOME | ||||||||
| A | B | C | D | |||||
| 2000 | Pine Bush | Cornwall | Liberty | SS Seward | ||||
| 2001 | Middletown | Onteora | Rhinebeck | Chester | ||||
| 2002 | Kingston | Monticello | Spackenkill | SS Seward | ||||
| 2003 | Kingston | Red Hook | Fallsburg FA | SS Seward | ||||
| AA | A | B | C | D | ||||
| 2004 | Kingston | Cornwall | Red Hook | Millbrook | SS Seward | |||
| 2005 | Monroe-Woodbury | Red Hook | Burke Catholic | Millbrook | SS Seward | |||
| 2006 | Newburgh FA | Red Hook | Spackenkill | Millbrook | Family School | |||
| 2007 | Newburgh FA | Cornwall | Burke Catholic | Tri-Valley | Coleman Catholic | |||
| 2008 | Minisiink Valley | New Paltz | Red Hook | Millbrook | Coleman Catholic | |||
| 2009 | Newburgh FA | Cornwall | Burke Catholic | Millbrook | Coleman Catholic | |||
| 2010 | Newburgh FA | Red Hook | Burke Catholic | SS Seward | Coleman Catholic | |||
| 2011 | Newburgh FA | Red Hook | Burke Catholic | Pine Plains | Coleman Catholic | |||
| 2012 | Middletown | Marlboro | Burke Catholic | Pine Plains | Livingston Manor | |||
| 2013 | Kingston | Burke Catholic | Marlboro | Pine Plains | Coleman Catholic | |||
| 2014 | Newburgh FA | Red Hook | Spackenkill | SS Seward | Coleman Catholic | |||
| 2015 | Middletown | Saugerties | Marlboro | Chester | Livingston Manor | |||
| 2016 | Middletown | Red Hook | Marlboro | Chester | Eldred | |||
| 2017 | Pine Bush | Poughkeepsie | Spackenkill | Millbrook | SS Seward | |||
| 2018 | Pine Bush | New Paltz | Marlboro | Millbrook | Livingston Manor | |||
| 2019 | Kingston | New Paltz | Ellenville | Millbrook | Roscoe | |||
| 2020 | Newburgh FA | New Paltz | Marlboro | Pine Plains | Livingston Manor | |||
| No Champions | ||||||||
| 2021 | x | |||||||
| AA | A | B | C | D | ||||
| 2022 | Newburgh FA | Goshen | Rondout Valley | Chester | Chapel Field | |||
| 2023 | Newburgh FA | Goshen | Burke | Rhinebeck | Chapel Field | |||
| AAA | AA | A | B | C | D | |||
| 2024 | Kingston | Lourdes | Saugerties | Burke | Millbrook | Chapel Field | ||
| 2025 | Newburgh FA | Lourdes | New Paltz | Burke | Mount Academy | Eldred | ||