| Dutchess County 2000-2024 | |||||||||||
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| Top Teams | Top Players | ||||||||||
| School | W | L | Class | Sect | Accomplishements | Player | School | Hgt | Class | College | |
| 2000 Poughkeepsie | 23 | 1 | A | 1 | Section 1 A Runnerup | Yamar Diene | Poughkeepsie | 6-9 | 2000 | Rice | |
| 2002 Poughkeepsie | 22 | 2 | A | 1 | Section 1 A Runnerup | Desham Allah | Poughkeepsie | G | 2000 | 1000 point scorer | |
| 2003 Red Hook | 21 | 3 | B | 9 | Section 9 B Champs | Edwin Ubiles | Poughkeepsie | 6-6 | 2004 | Transferred to St. Thomas More as a senior / Siena | |
| 2003 Beacon | 20 | 5 | A | 1 | State B Semifinals | Melquan Bolding | Beacon | 6-3 | 2004 | Transferred to Stepinac as a Soph / Duquesne | |
| 2004 Red Hook | 22 | 2 | A | 9 | Section 9 B Champs | Will Daniels | FDR | 6-7 | 2004 | 1000 point scorer / Rhode Island | |
| 2005 Red Hook | 22 | 2 | A | 9 | Section 9 A Champs | Lamar Pittman | Poughkeepsie | 6-8 | 2005 | North Carolina Central | |
| 2005 Poughkeepsie | 20 | 3 | AA | 1 | Section 1 AA Semifinals | Zach Wing | Lourdes | 6-7 | 2005 | Fordham | |
| 2006 Red Hook | 22 | 2 | A | 9 | Section 9 A Champs | Greg Nero | Red Hook | 6-7 | 2006 | 1000 point scorer / Fairfield | |
| 2006 Poughkeepsie | 20 | 3 | AA | 1 | Section 1 AA Semifinals | Tyquan Stroman | Poughkeepsie | 6-6 | 2006 | St. Augustine | |
| 2007 Poughkeepsie | 20 | 3 | AA | 1 | Section 1 AA Semifinals | Antonio Williams | Poughkeepsie | 6-6 | 2008 | Coppin St. | |
| 2008 Poughkeepsie | 20 | 4 | AA | 1 | Section 1 AA Runnerup | Brandon James | Poughkeepsie | 6-6 | 2009 | Colgate | |
| 2009 Poughkeepsie | 20 | 3 | AA | 1 | Section 1 AA Runnerup | Dayvon Whitaker | Poughkeepsie | 5-9 | 2010 | Manhattan | |
| 2010 Red Hook | 23 | 1 | A | 9 | State A Semifinals | Nate Gause | Poughkeepsie | 6-5 | 2011 | 1000 point scorer / LeMoyne | |
| 2010 Poughkeepsie | 20 | 2 | AA | 1 | Section 1 AA Runnerup | Tyler Lydon | Pine Plains | 6-7 | 2013 | New Hampton senior year / Syracuse / Denver Nuggets | |
| 2011 Poughkeepsie | 21 | 1 | AA | 1 | Section 1 A Runnerup | Elijah Hughes | Beacon | 6-4 | 2014 | Transferred to JFK as a Junior / Syracuse / Utah Jazz | |
| 2011 Red Hook | 19 | 3 | A | 9 | State A Semifinals | James Anozie | Poughkeepsie / Lourdes | 6-6 | 2017 | 1000 Point Scorer / Keene St | |
| 2012 Pine Plains | 19 | 3 | C | 9 | Section 9 C Champs | Alpha Bangura | RCK | 6-8 | 2018 | Transferred to Stepinac as a Junior | |
| 2013 Pine Plains | 21 | 3 | C | 9 | State C Runnerup | Aiden Hilderbrand | JJEF | 6-4 | 2018 | Transferred to Iona Prep as a junior / Pace | |
| 2013 Poughkeepsie | 19 | 3 | A | 1 | Section 1 A Champs | Aaron Davis | Beacon | 5-10 | 2019 | Buffalo St | |
| 2014 Red Hook | 17 | 6 | A | 9 | State A Semifinals | Brandon Cahill | Red Hook | 6-1 | 2020 | Castleton St | |
| 2015 Arlington | 20 | 1 | AA | 1 | Section 1 AA Semifinals | Shaun Johnson | Poughkeepsie | 6-2 | 2020 | SUNY Cobbleskill | |
| 2017 Spackenkill | 20 | 3 | B | 9 | Section 9 B Champs | Shelvon Grant | Poughkeepsie | 6-4 | 2020 | SUNY Cobbleskill | |
| 2017 Lourdes | 20 | 7 | A | 1 | State Class A Runnerup | Javel Cherry | Poughkeepsie | 6-2 | 2021 | Dominican | |
| 2019 Poughkeepsie | 25 | 4 | A | 1 | State A Champs | Zaccai Curtis | Poughkeepsie | 6-3 | 2021 | ||
| 2020 Poughkeepsie | 17 | 7 | A | 1 | Section 1 A Runnerup | Dejon Hamilton | Poughkeepsie | 6-6 | 2021 | Western Connecticut St | |
| 2021 FDR | 6 | 0 | 9 | MHAL Dutchess Champ | Delano Knox | Arlington | 6-4 | 2022 | Oneonta St | ||
| 2021 Poughkeepsie | 11 | 2 | AA | 1 | Dutchess Sect 1 Champ | Jaysean Morgan | Poughkeepsie | 6-2 | 2022 | Western Connecticut St | |
| 2022 Poughkeepsie | 18 | 8 | AA | 1 | State A Semifinals | Jahlyl Morgan | Poughkeepsie | 6-2 | 2022 | Western Connecticut St | |
| 2022 Lourdes | 18 | 6 | AA | 1 | Sect 1 A Runnerup | Chris Faughnan | Lourdes | 6-5 | 2022 | RPI | |
| 2022 Rhinebeck | 16 | 7 | C | 9 | Sect 9 C Semifinals | Bryce Aierstok | Rhinebeck | 6-4 | 2022 | Pace | |
| 2022 Arlington | 15 | 8 | AA | 1 | Sect 1 AA Semifnals | Dylan Howard | Beacon | 6-4 | 2023 | ||
| 2023 Spackenkill | 17 | 5 | B | 9 | Section 9 B Semifinals | Owen Paino | RCK | 6-3 | 2024 | Baseball | |
| 2023 Lourdes | 17 | 6 | A | 9 | Section 9 A Runnerup | Patrick Faughnan | Lourdes | 6-5 | 2024 | Injured | |
| 2023 Beacon | 15 | 7 | A | 9 | Section 9 A Semifinals | ||||||
| 2023 Rhinebeck | 13 | 7 | C | 9 | Section 9 C Champs | ||||||
| 2024 Lourdes | 19 | 5 | AA | 9 | State AA Semis | ||||||
| 2024 Spackenkill | 17 | 4 | A | 9 | Sect 9 A Semis | ||||||
| 2024 Beacon | 14 | 9 | A | 9 | Sect 9 A Runnerup | ||||||