| Season | Winner |
| 1995-96 | M Mucenieks |
| 1996-97 | L Prince |
| 1997-98 | A Gregory |
| 1998-99 | L Gill |
| 1999-00 | P Barker |
| 2000-01 | R Denovan |
| 2001-02 | S McCleary |
| 2002-03 | R Denovan |
| 2003-04 | A Patton |
| 2004-05 | L Gill |
| 2005-06 | T McKenna |
| 2006-07 | S Daly |
| 2007-08 | J Barker |
| 2008-09 | P Clancey |
| 2009-10 | P Clancey |
| 2010-11 | J Barker |
| 2011-12 | S McCleary |
| 2012-13 | S McCleary |
| 2013-14 | P Cutter |
| 2014-15 | S Muthumuni |
| 2015-16 | P Sparks |
| 2016-17 | A Christie |
| 2017-18 | P Sparks |
| 2018-19 | R Symons |
| 2019-20 | D Clarke |
Trinity Willison Cricket ClubEst. 1935