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Tamerlane's forces defeat the Ottoman empire, briefly interrupting Ottoman power.

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In 1345 the Dardanelles, acquired their first foothold in Europe by capturing Gallipoli which later lead to Bulgaria becoming part of their growing empire in 1393.

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The Christian Navy defeats the Ottoman Navy at the battle of Lepanto, one of the last battles between galley fleets in Europe.

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In 1453 the Ottomans eded the 1,100-year byzantine empire by overrunning constantinople

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From 1299-1326 Osman I begins the Ottoman dynasty as he declares independence from the Seljuk Turks. Conquest of Bursa and the emirate of Karasi brought Osman and his heirs to the Mediterranean. A little later, in 1393, Bulgaria became a part of their empire.

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See a newer updated and more accurate one here: https://www.youtube.com/watch?v=YPkbJPguPn8