Winners of all times
| 1996 | Ille Kukk | 00:26:44 |
| 1997 | Saimi Pevkur | 00:26:09 |
| 1998 | Jane Salumäe | 00:22:50 |
| 1999 | Jane Salumäe | 00:23:21 |
| 2000 | Maile Mangusson | 00:24:22 |
| 2001 | Maile Mangusson | 00:24:22 |
| 2002 | Maile Mangusson | 00:24:01 |
| 2003 | Maile Mangusson | 00:25:05 |
| 2004 | Kadri Kelve | 00:24:55 |
| 2005 | Maile Mangusson | 00:25:04 |
| 2006 | Julia Bulina | 00:24:49 |
| 2007 | Liina Tšernov | 00:18:19 |
| 2008 | Liina Tšernov | 00:24:59 |
| 2009 | Evelin Kärner | 00:25:44 |
| 2010 | Evelin Kärner | 00:24:29 |
| 2011 | Jekaterina Patjuk | 00:23:15 |
| 2012 | Jekaterina Patjuk | 00:25:37 |
| 2013 | Liina Tšernov | 00:23:24 |
| 2014 | Jekaterina Patjuk | 00:22:43 |
| 2015 | Jekaterina Patjuk | 00:23:00 |
| 2016 | Liina Tšernov | 00:23:35 |
| 2017 | Liina Tšernov | 00:23:08 |
| 2018 | Liina Tšernov | 00:23:28 |
| 2019 | Liina Tšernov | 00:23:22 |
| 2020 | Maijooks took place virtually | |
| 2021 | Maijooks took place virtually | |
| 2022 | Laura Maasik | 00:24:43 |
| 2023 | Laura Maasik | 00:23:23 |
1988-1995 Maijooks had running and walking events that were not timed. No winners were announced.
