| 2024/25 | Kellie Hands Cert CII, MInstLM | Tower Insurance Company Ltd |
| 2023/24 | John Walker DipPFS, CertPFS (DM) | LMS Partners Limited |
| 2022/23 | John Walker DipPFS, CertPFS (DM) | LMS Partners Limited |
| 2021/22 | Gillian Marples Cert CII | IntegraLife International Limited |
| 2020/21 | Gillian Marples Cert CII | IntegraLife International Limited |
| 2019/20 | Sandra Cardwell DipPFS, Cert IoD | Edgewater Associates Limited |
| 2018/19 | Sandra Cardwell DipPFS, Cert IoD | Edgewater Associates Limited |
| 2017/18 | Matthew Hills ACII, Cert IRM | Aon Insurance Managers (IOM) Ltd |
| 2016/17 | Peter Gallagher MBA, FCII, Chartered Insurer | Tower Insurance Company Ltd |
| 2015/16 | Bryan O'Connor ACSI, Dip CII | Edgewater Associates Limited |
| 2014/15 | John Hockney APFS, Chartered Financial Planner | Hockney Stevens Investment Services |
| 2013/14 | Oriana Hills FICA | Isle of Man Financial Services Authority |
| 2012/13 | Karen Ladly ACSI, ACII, Chartered Insurance Practitioner | Isle of Man Financial Services Authority |
| 2011/12 | Sharon Sutton APFS, Chartered Financial Planner | Thornton Associates Ltd |
| 2010/11 | Nick Boon ACII | Isle of Man Finance |
| 2009/10 | Sue Gee CertPFS | TLC Business Solutions Ltd |
| 2008/09 | Emmet McQuillan ACII | Tower Insurance Company Ltd |
| 2007/08 | Philip Angus | Marsh (Isle of Man ) Ltd |
| 2006/07 | Kevin Wood Cert PFS | Investasure Financial Services Ltd |
| 2005/06 | Adrienne Thompson ACII | AXA Isle of Man Ltd |
| 2004/05 | Paul Ellison ACII | Scottish Provident International |
| 2003/04 | Lillian Boyle FCII | Scottish Provident International |
| 2002/03 | David Stacey FCII | Tower Insurance Company Ltd |
| 2001/02 | Denise Goodburn ACII | Hansard International Ltd |
| 2000/01 | Alan Holdsworth | Marsh Management Services Ltd |
| 1999/00 | Martin Rosevear | Marsh (Isle of Man) Ltd |
| 1998/99 | Colin Curphey | Thomas Howell Loss Adjusters |
| 1997/98 | Wendy Sayer LLB Hons, ACII | Aon Insurance Managers Ltd |
| 1996/97 | Rod Jones ACII | J M Pearson & Co Ltd |
| 1995/96 | Bob Martin | Sedgewicks |
| 1994/95 | David Vick ACII | Isle of Man Financial Services Authority |
| 1993/94 | Jim Hardie ACII | Eagle Star |
| 1992/93 | Glyn Gilbert ACII | Tower Insurance Company Ltd |
| 1991/92 | Christine Crowther FCII | Castletown Insurance Ltd |
| 1990/91 | John Booth ACII | Commercial Union |
| 1989/90 | Les Doherty | Marsh (Isle of Man) Ltd |
| 1988/89 | Richard Gough FCII | Royal Life International |
| 1987/88 | Michael Linck FCII | Sedgewicks |
