According to one implementation, a damage detection system includes: a physical quantity detection unit, a flight condition changing part and a damage detection part. The physical quantity detection unit detects a physical quantity of a structural object composing an aircraft during a flight of the aircraft. The flight condition changing part changes at least one flight condition of the aircraft to at least one specific flight condition when the physical quantity of the structural object has been detected by the physical quantity detection unit. The damage detection part determines whether a damage arose in the structural object, based on a physical quantity which has been detected, from the structural object of the aircraft flying with the at least one specific flight condition, by the physical quantity detection unit.