| Year | Senior Winner | Site |
|---|---|---|
| 2024 | Herrol Pryce | Tamarack |
| 2023 | Ned Zachar | GlenArbor |
| 2022 | Ken Cohen | Metropolis |
| 2021 | Drew Greenland | Paramount |
| 2020 | No Championship | |
| 2019 | Tom Yellin | Winged Foot |
| 2018 | Tom Yellin | Brooklawn |
| 2017 | Jim Romaniello | Whippoorwill |
| 2016 | Jon Groveman | Ardsley |
| 2015 | Richard Feldman | Rockrimmon |
| 2014 | James Romaniello | Westchester CC |
| 2013 | Jim Graham | Brae Burn |
| 2012 | Jon Groveman | Rockrimmon |
| 2011 | Joe Sommers | Trump Hudson Valley |
| 2010 | Jon Groveman | Woodway |
| 2009 | Jim Graham | Fairview |
| 2008 | Robert Howe | Rockrimmon |
| 2007 | Robert Howe | Stanwich |
| 2006 | George Riehm | Sleepy Hollow |
| 2005 | Shawn McLoughlin | Sunningdale |
| 2004 | Robert Stuart | Metropolis |
| 2003 | Bill Dober | Woodway |
| 2002 | John Baer | Fenway |
| 2001 | Dave Saunders | Knollwood |
| 2000 | Tom Jung | Tamarack |
| 1999 | Richard Suggs | Old Oaks |
| 1998 | John Pretak | Fenway |
| Year | Super Senior Winner | Site |
|---|---|---|
| 2024 | Mark Vassalotti | Tamarack |
| 2023 | Mark Vassalotti | GlenArbor |
| 2022 | Rick Blank | Metropolis |
| 2021 | Rick Blank | Paramount |
| 2020 | No Championship | |
| 2019 | Bill Dober | Winged Foot |
| 2018 | Rick Blank | Brooklawn |
| 2017 | Russ Sirico | Whippoorwill |
| 2016 | Shawn McLoughlin | Ardsley |
| 2015 | Shawn McLoughlin | Rockrimmon |
| 2014 | Shawn McLoughlin | Westchester CC |
| 2013 | Frank Ciulla | Brae Burn |
| 2012 | Peter Friedes | Rockrimmon |
| 2011 | John Zygmunt | Trump Hudson Valley |
| 2010 | Peter Friedes | Woodway |
| 2009 | Peter Friedes | Fairview |
| 2008 | Peter Friedes | Rockrimmon |
| 2007 | Ray Darmstadt, Jr. | Stanwich |
| 2006 | Ray Darmstadt, Jr. | Sleepy Hollow |
| 2005 | Ray Darmstadt, Jr. | Sunningdale |
| 2004 | Jay FitzGerald | Metropolis |
| 2003 | Joe Cerniglia | Woodway |
| 2002 | Arnold Lipman | Fenway |
| 2001 | Frank Petrocelli | Knollwood |
