| Year | Contest Winner | Club | Division | |
| D91 | ||||
| 2022-2023 | Dan Magill | Croydon Communicators | L | |
| 2021-2022 | Dan Magill | Society Speakers, Croydon Communicators | L | |
| 2020-2021 | Shivpriya Gowri | Purley Speakers | H | |
| 2019-2020 | Paola Podesta | London Olympians | B | |
| 2018-2019 | Daniel Magill | Epsom Speakers | H | |
| 2017-2018 | Ola Aralepo | Tube Talk | C | |
| 2016-2017 | Dallas Leigh-Martene | London Olympians | B | |
| 2015-2106 | Selina Jones | Aylesbury Speakers | A | |
| 2014-2015 | Tazud Miah | Early Bird Speakers | B |
| Year | Contest Winner | Club |
| D71 | ||
| 2013 | Brian Faulkner | Speak Easy @Martlesham Speakers’ Club |
| 2012 | Tania West | South West Speakers |
| 2011 | Ola Aralepo | Tube Talk Toastmasters |
| 2010 | Adam Broomfield-Straun | Arun Speakers |
| 2009 | Bob Ferguson | Excalibur Speakers |
| 2008 | Michael Cronin | Speakeasy, Cork |
| 2007 | Bev Avis-Dakin | Spa Speakers |
| 2006 | Cole McInnes | London Cardinals |
| 2005 | Gerry French | Fingal Toastmasters Club |
| 2004 | Noreen McSweeney | Muskerry Toastmasters |
| 2003 | Chris Cox | Cambridge Speakers |
| 2002 | C. Blair | Engineers Club |
| 2001 | Aileen Bennett | London Corinthians |
| 2000 | Andrew Brammer | Norwich Speakers |
| 1999 | Ray Cotter | Lucan Club |
| 1998 | Siobhan O’Connor | Castleknock Toastmasters Club |
| 1996 | David O’Keefe | Cork |
| 1995 | Matt Lawlee | Speakeasy, Cork |
| 1994 | Brendan Toale | Glasnevin Club |
| 1993 | Liam Grimes | Fingal Toastmasters Club |
| 1992 | Gerry Moran | Kilkenny Club |
| 1991 | Mary O’Reilly | Hellfire Club |
| 1990 | Noel O’Beara | Fingal Toastmasters Club |
| 1989 | Niall Blake | Ennis Toastmasters Club |
| 1988 | Ted Corcoran | Fingal Toastmasters Club |
| 1987 | David Lindsey | Thame Speakers |