Winners
| Year | Winner | Opponent |
|---|---|---|
| 1995 | Martin Reim |  Slovenia
|
| 1996 | Argo Arbeiter |  Andorra
|
| 1997 | Martin Reim (2) |  Lithuania
|
| 1998 | Sergei Terehhov |  Faroe Islands
|
| 1999 | Martin Reim (3) | Faroe Islands
|
| 2000 | Indrek Zelinski |  Hong Kong
|
| 2001 | Andres Oper |  Netherlands
|
| 2002 | Teet Allas |  Moldova
|
| 2003 | Indrek Zelinski (2) | Andorra
|
| 2004 | Kristen Viikmäe |  Liechtenstein
|
| 2005 | Andres Oper (2) |  Slovakia
|
| 2006 | Tarmo Neemelo |  Turkey
|
| 2007 | Indrek Zelinski (3) | Andorra
|
| 2008 | Vjatšeslav Zahovaiko | Faroe Islands
|
| 2009 | Konstantin Vassiljev |  Armenia
|
| 2010 | Tarmo Kink |  Serbia
|
| 2011 | Konstantin Vassiljev (2) |  Northern Ireland
|
| 2012 | Konstantin Vassiljev (3) |  Poland
|
| 2013 | Konstantin Vassiljev (4) | Netherlands
|
| 2014 | Siim Luts |  Tajikistan
|
| 2015 | Sander Puri |  Saint Kitts and Nevis
|
| 2016 | Konstantin Vassiljev (5) |  Gibraltar
|
| 2017 | Mattias Käit |  Cyprus
|
| 2018 | Siim Luts (2) |  Hungary
|
| 2019 | Konstantin Vassiljev (6) | Northern Ireland
|
| 2020 | Rauno Sappinen |  North Macedonia
|
| 2021 | Mattias Käit (2) |  Belgium
|
| 2022 | Konstantin Vassiljev (7) |  Malta
|
