| # | Tulemus | Sportlane | Võistlus | Vanuseklass | Linn | Kuupäev | ||
|---|---|---|---|---|---|---|---|---|
| 1911 | 2:10:55 | Kristi Oras, 1975 | Tartu rattaralli (64 km) | N50-54 | Tartu | 01.06.25 | ||
| 1912 | 2:11:04 | Mirko Talu, 1985 | Mulgi rattamaraton (47 km) | M40-44 | Viljandi | 04.05.25 | ||
| 1913 | 2:11:05 | Allan Jõgi, 1981 | Mulgi rattamaraton (47 km) | M40-44 | Viljandi | 04.05.25 | ||
| 1914 | 2:11:05 | Andres Pool, 1966 | Tartu rattaralli (64 km) | M55-59 | Tartu | 01.06.25 | ||
| 1915 | 2:11:16 | Krister Paris, 1977 | Tartu rattaralli (64 km) | M45-49 | Tartu | 01.06.25 | ||
| 1916 | 2:11:19 | Madis Sildvee, 1978 | Mulgi rattamaraton (47 km) | M45-49 | Viljandi | 04.05.25 | ||
| 1917 | 2:11:20 | Alar Reiska, 1963 | Mulgi rattamaraton (47 km) | M60-64 | Viljandi | 04.05.25 | ||
| 1918 | 2:11:24 | Jürgen Lukkanen, 1996 | Tartu rattaralli (64 km) | M23-34 | Tartu | 01.06.25 | ||
| 1919 | 2:11:34 | Artur Teearu, 2016 | Mulgi rattamaraton (22 km) | M8-9 | Viljandi | 04.05.25 | ||
| 1920 | 2:11:35 | Paul Teearu, 1989 | Mulgi rattamaraton (22 km) | M35-39 | Viljandi | 04.05.25 |