| Year | Team Name | Manager |
|---|---|---|
| 2021-22 | Rippers | Jay Sill & Rob Holzman |
| 2019-20 | Rippers | Jay Sill & John Murk |
| 2018-19 | JACKSOX | Jack Allegretti & Mike Call |
| 2017-18 | Sleeves | Steve Leslie & Pat Bergman |
| 2016-17 | The Crew | Kirk Dunning & Jamie Hughes |
| 2015-16 | Rippers | Jay Sill & Bob Shepro |
| 2014-15 | Rippers | Jay Sill & Bob Shepro |
| 2013-14 | Rippers | Jay Sill & Bob Shepro |
| 2012-13 | Surf Dawgs | Andy Mercer & Ken MacDonald |
| 2011-12 | Red Tide | Frank Kuzinar & Jason Haines |
| 2010-11 | Surf Dawgs | Andy Mercer & Ken MacDonald |
| 2009-10 | Rippers | Jay Sill & Bob Shepro |
| 2008-09 | Mad Men | Gary Nugent |
| 2007-08 | Orange Crush | Jim Lindsay |
| 2006-07 | Mangy Marauders | Tim Thompson |
| 2005-06 | Mangy Marauders | Tim Thompson |
| 2004-05 | Mangy Marauders | Tim Thompson |
| 2003-04 | Blues | Steve Leslie & John Lester |
| 2002-03 | Yellow Jackets | Daryl Wasano |
| 2001-02 | The Patriots | Howard Wiedre |
| 2000-01 | The Better I Was | Jim Youngs |
| 1999-2000 | Unknown | |
| 1998-99 | Dirty Dozen | Bill Bicknell |
| 1997-98 | La Costa Gold | David Cain |
| 1996-97 | Canardlies | Jeff Walker |
| 1995-96 | No winter league play | |
| 1994-95 | No winter league play | |
| 1993-94 | Unknown | |
| 1992-93 | Angels | Gene Hallner & Gary Nugent |
| 1991-92 | Giants | Wayne Woods |
| 1990-91 | Mets | |
| 1989-90 | Dodgers | Jim Works |
| 1988-89 | Jitterbugs | |
| 1987-88 | Alley-Oops | Gene Hallner |
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