The oldest known picture of 'Dannebrog' (the Danish flag) appeared in the coat of arms of the kings of Denmark in the late fourteenth century.

According to the chroniclers, Dannebrog fell from the heavens during the battle at Lyndanise near Reval in Estonia in 1219, and it brought victory to the Danes under king Valdemar II ('the Victorious'). The story goes that Anders Suneson, the fighting bishop in the king's army, stood with his arms lifted towards heaven during the entire battle. Whenever he tired, and his arms came down, the Danes did not do well, and eventually two helpers held up his arms. That was when the Maltese cross banner descended from above and the victory was ensured.

Four years later, Valdemar and his son Valdemar the Young were taken prisoners by Count Heinrich of Schwerin and as a condition for the release of the royal hostages Denmark had to give up all its Baltic possessions save Ruegen and Estonia. Valdemar tried once more to win back the lost possessions, but for the first time ever he tasted defeat, at Bornhoeved on 22 July 1227.

Estonia remained a part of Denmark until 1346 when the territory was sold by King Valdemar 'Atterdag' to the German Order of Knights, a confederation of German pilgrims and merchants with headquarters in Kønigsberg.

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