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| Champions | # | Last | Cup Winners | # | Last | |||
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| 1 | FC Flora Tallinn | 15 | 2023 | 1 | FCI Levadia Tallinn | 12 | 2021 | |
| 2 | FCI Levadia Tallinn | 10 | 2021 | 2 | FC Flora Tallinn | 8 | 2020 | |
| 3 | JK Nõmme Kalju | 2 | 2018 | 3 | JK Narva Trans | 3 | 2023 | |
| 4 | FC Lantana Tallinn † | 2 | 1997 | 4 | FC TVMK Tallinn † | 2 | 2006 | |
| 5 | FC Norma Tallinn † | 2 | 1993 | 5 | JK Nõmme Kalju | 1 | 2015 | |
| 6 | FC TVMK Tallinn † | 1 | 2005 | 6 | FC Lantana Tallinn † | 1 | 1993 | |
| 7 | FCI Tallinn † | 1 | 2016 | 7 | Paide Linnameeskond | 1 | 2022 | |
| 8 | FC Norma Tallinn † | 1 | 1994 | |||||
| 9 | FCI Tallinn † | 1 | 2017 | |||||
| 10 | FC Levadia-2 Tallinn | 1 | 2002 |
| Year | Champions | Runners-up | Third | Cup Winners |
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| 2023 # | FC Flora Tallinn | FCI Levadia Tallinn | JK Tallina Kalev | JK Narva Trans |
| 2022 # | FC Flora Tallinn | FCI Levadia Tallinn | Paide Linnameeskond | Paide Linnameeskond |
| 2021 # | FCI Levadia Tallinn | FC Flora Tallinn | Paide Linnameeskond | FCI Levadia Tallinn |
| 2020 # | FC Flora Tallinn | Paide Linnameeskond | FCI Levadia Tallinn | FC Flora Tallinn |
| 2019 # | FC Flora Tallinn | FCI Levadia Tallinn | JK Nõmme Kalju | JK Narva Trans |
| 2018 # | JK Nõmme Kalju | FCI Levadia Tallinn | FC Flora Tallinn | FCI Levadia Tallinn |
| 2017 # | FC Flora Tallinn | FCI Levadia Tallinn | JK Nõmme Kalju | FCI Tallinn † |
| 2016 # | FCI Tallinn † | FCI Levadia Tallinn | JK Nõmme Kalju | FC Flora Tallinn |
| 2015 # | FC Flora Tallinn | FCI Levadia Tallinn | JK Nõmme Kalju | JK Nõmme Kalju |
| 2014 # | FCI Levadia Tallinn | JK Sillamäe Kalev | FC Flora Tallinn | FCI Levadia Tallinn |
| 2013 # | FCI Levadia Tallinn | JK Nõmme Kalju | JK Sillamäe Kalev | FC Flora Tallinn |
| 2012 # | JK Nõmme Kalju | FCI Levadia Tallinn | FC Flora Tallinn | FCI Levadia Tallinn |
| 2011 # | FC Flora Tallinn | JK Nõmme Kalju | JK Narva Trans | FC Flora Tallinn |
| 2010 # | FC Flora Tallinn | FCI Levadia Tallinn | JK Narva Trans | FCI Levadia Tallinn |
| 2009 # | FCI Levadia Tallinn | JK Sillamäe Kalev | JK Narva Trans | FC Flora Tallinn |
| 2008 # | FCI Levadia Tallinn | FC Flora Tallinn | FC TVMK Tallinn † | FC Flora Tallinn |
| 2007 # | FCI Levadia Tallinn | FC Flora Tallinn | FC TVMK Tallinn † | FCI Levadia Tallinn |
| 2006 # | FCI Levadia Tallinn | JK Narva Trans | FC Flora Tallinn | FC TVMK Tallinn † |
| 2005 # | FC TVMK Tallinn † | FCI Levadia Tallinn | JK Narva Trans | FCI Levadia Tallinn |
| 2004 # | FCI Levadia Tallinn | FC TVMK Tallinn † | FC Flora Tallinn | FCI Levadia Tallinn |
| 2003 # | FC Flora Tallinn | FC TVMK Tallinn † | FCI Levadia Tallinn | FC TVMK Tallinn † |
| 2002 # | FC Flora Tallinn | FCI Levadia Tallinn | FC TVMK Tallinn † | FC Levadia-2 Tallinn |
| 2001 # | FC Flora Tallinn | FC TVMK Tallinn † | FCI Levadia Tallinn | JK Narva Trans |
| 2000 # | FCI Levadia Tallinn | FC Flora Tallinn | FC TVMK Tallinn † | FCI Levadia Tallinn |
| 1999 # | FCI Levadia Tallinn | JK Tulevik Viljandi | FC Flora Tallinn | FCI Levadia Tallinn |
| 1998 | FC Flora Tallinn | FCI Levadia Tallinn | FC Lantana Tallinn † | --- |
| 1997/98 | FC Flora Tallinn | FCI Levadia Tallinn | FC Lantana Tallinn † | FC Flora Tallinn |
| 1996/97 | FC Lantana Tallinn † | FC Flora Tallinn | FCI Levadia Tallinn | FCI Levadia Tallinn |
| 1995/96 | FC Lantana Tallinn † | FC Flora Tallinn | FC TVMK Tallinn † | FCI Levadia Tallinn |
| 1994/95 | FC Flora Tallinn | FC Lantana Tallinn † | JK Narva Trans | FC Flora Tallinn |
| 1993/94 | FC Flora Tallinn | FC Norma Tallinn † | FC Lantana Tallinn † | FC Norma Tallinn † |
| 1992/93 | FC Norma Tallinn † | FC Flora Tallinn | FC Lantana Tallinn † | FC Lantana Tallinn † |
| 1992 | FC Norma Tallinn † | JK Eesti Põlevkivi Jõhvi † | FC Lantana Tallinn † | --- |