[2] The fortress was founded by Erik Axelsson Tott in 1475 under the name Sankt Olofsborg in an effort to profit from the political turmoil following Ivan III's conquest of the Novgorod Republic.

[3][4][5][6] One of Tott's letters from 1477 includes a passing mention of foreign builders invited to Olofsborg, probably from Reval, where the city fortifications were being extended.

A brisk trade developed under the umbrella of the castle towards the end of the 16th century, giving birth to the town of Savonlinna, which was chartered in 1639.

[8] After the conclusion of the Russo-Swedish War 1495-1497, Sten Sture returned to Sweden and discovered that a large revolt had begun against him, resulting in the Battle of Rotebro where he was deposed in favor of King Hans of Denmark.

Despite this, there was no guaranteed peace on the border between them, and among other things a letter from 1509 tells that "the enemies of God and Christendom, the intransigent Russians" have ravaged Finland.

Olavinlinna is the initial model for Kropow Castle in the bande dessinée King Ottokar's Sceptre, an album in the series of Adventures of Tintin created by Hergé.