Arnold Rüütel People's Union Toomas Hendrik Ilves Social Democratic Estonian presidential elections, 2006 took place over four rounds, which were held on 28 and 29 August,[1] and 23 September 2006.

The two top candidates, Ene Ergma and Toomas Hendrik Ilves, were not elected because they did not obtain the required two-thirds of the votes in the Riigikogu.

It was convened on 23 September, and Toomas Hendrik Ilves emerged as the winner over the other candidate and incumbent president, Arnold Rüütel, after obtaining a majority of the votes in the electoral college.

[3] The President of the Republic of Estonia is indirectly elected, and serves primarily to represent the country as the symbolic Head of State of the executive branch.

Any Estonian citizen by birth over the age of forty can be nominated as a candidate, but must be supported by a minimum of one fifth of the Riigikogu, equivalent to 21 members.

On 11 May Laine Jänes, Liina Tõnisson, Peeter Tulviste, Jaan Männik, and Toomas Varek were eliminated from the race.

Though, according to analysts, Rüütel had high chances in the electoral college and was supported by the People's Union and the Centre Party, he was constantly criticized for not having participated in the Riigikogu round and not taking part in debates.

The end of his term was overshadowed by a scandalous story shown on the Estonian Television about Rüütel's teenage granddaughters running orgies in the presidential palace.

His victory in the 2006 presidential election, that was named "clash of the eras", was regarded partially as a protest against the parties that supported Rüütel and as a rejection of the Soviet-era leader in favor of youthful and more liberal president.