The oldest Kruispoort gate was built during the second city wall (1297-1304) and was already replaced in 1366. When Philip of Artevelde took the city with the people of Ghent in 1382, he destroyed the gate. In 1400, gate number three followed. Only the two heavy towers with their narrow passage and two octagonal turrets were preserved.
Charles V, Napoleon, the German army - they all entered the city of Bruges through this gate.