The first Kruispoort gate was built simultaneously with the second rampart (1297-1304) and already rebuilt in 1366. Philip van Artevelde destroyed the gate when he captured the city with the Ghent militia in 1382. In 1400 the third gate was constructed. Only the two heavy towers with their narrow passage and two octagonal turrets were preserved. Holy Roman Emperor Charles V, Napoleon and the German army all entered Bruges through this gate.